DK142027B - Fremgangsmåde til fremstilling af substituerede methoxyaminer. - Google Patents
Fremgangsmåde til fremstilling af substituerede methoxyaminer. Download PDFInfo
- Publication number
- DK142027B DK142027B DK66872A DK66872A DK142027B DK 142027 B DK142027 B DK 142027B DK 66872 A DK66872 A DK 66872A DK 66872 A DK66872 A DK 66872A DK 142027 B DK142027 B DK 142027B
- Authority
- DK
- Denmark
- Prior art keywords
- preparation
- substituted
- phthalimide
- reacted
- hydrochloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 52
- 238000002360 preparation method Methods 0.000 title description 48
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical class CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 title description 18
- -1 O-substituted hydroxylamine compounds Chemical class 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000354 decomposition reaction Methods 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 230000001476 alcoholic effect Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006698 hydrazinolysis reaction Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 150000003141 primary amines Chemical class 0.000 description 9
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 8
- 229960001814 trypan blue Drugs 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- LKCAFSOYOMFQSL-UHFFFAOYSA-N hydron;o-[(4-nitrophenyl)methyl]hydroxylamine;chloride Chemical compound Cl.NOCC1=CC=C([N+]([O-])=O)C=C1 LKCAFSOYOMFQSL-UHFFFAOYSA-N 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical compound ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- VGEWEGHHYWGXGG-UHFFFAOYSA-N ethyl n-hydroxycarbamate Chemical compound CCOC(=O)NO VGEWEGHHYWGXGG-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- YXLOBCKDORBZSN-UHFFFAOYSA-N methyl 3-(aminooxymethyl)-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(CON)=C1 YXLOBCKDORBZSN-UHFFFAOYSA-N 0.000 description 4
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- PLNOXXFMIVONEL-UHFFFAOYSA-N 2-(pyridin-3-ylmethoxy)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCC1=CC=CN=C1 PLNOXXFMIVONEL-UHFFFAOYSA-N 0.000 description 3
- KICBTWPSVKJQLP-UHFFFAOYSA-N 2-[(4-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1CON1C(=O)C2=CC=CC=C2C1=O KICBTWPSVKJQLP-UHFFFAOYSA-N 0.000 description 3
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 150000002443 hydroxylamines Chemical class 0.000 description 3
- 229960005192 methoxamine Drugs 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- ASEXCDTZEMCCTB-UHFFFAOYSA-N o-(pyridin-3-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=CN=C1 ASEXCDTZEMCCTB-UHFFFAOYSA-N 0.000 description 3
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical class NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 229920006395 saturated elastomer Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VJEZYZLITKUTFH-UHFFFAOYSA-N 2-(hydrazinecarbonyl)benzoic acid Chemical compound NNC(=O)C1=CC=CC=C1C(O)=O VJEZYZLITKUTFH-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- IOZADUIJKWISQS-UHFFFAOYSA-N 2-phenylmethoxyisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCC1=CC=CC=C1 IOZADUIJKWISQS-UHFFFAOYSA-N 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XCZJTACOXIZLBD-UHFFFAOYSA-N methyl 3-[(1,3-dioxoisoindol-2-yl)oxymethyl]-4-hydroxybenzoate Chemical compound OC1=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=C(C=C1)C(=O)OC XCZJTACOXIZLBD-UHFFFAOYSA-N 0.000 description 2
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 2
- KPTCZURLWZSRKB-UHFFFAOYSA-N o-prop-2-enylhydroxylamine Chemical compound NOCC=C KPTCZURLWZSRKB-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- UGFYBIIUXQGMSE-UHFFFAOYSA-N 2-(1h-imidazol-5-ylmethoxy)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCC1=CNC=N1 UGFYBIIUXQGMSE-UHFFFAOYSA-N 0.000 description 1
- KHLCHQITTKZTBX-UHFFFAOYSA-N 2-(hydroxycarbamoyl)benzoic acid Chemical class ONC(=O)C1=CC=CC=C1C(O)=O KHLCHQITTKZTBX-UHFFFAOYSA-N 0.000 description 1
- FLLMEVNTBYMHOD-UHFFFAOYSA-N 2-(pyridin-2-ylmethoxy)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCC1=CC=CC=N1 FLLMEVNTBYMHOD-UHFFFAOYSA-N 0.000 description 1
- OKRVKSFMNWUJGJ-UHFFFAOYSA-N 2-(pyridin-4-ylmethoxy)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCC1=CC=NC=C1 OKRVKSFMNWUJGJ-UHFFFAOYSA-N 0.000 description 1
- QVMAVYVJYYXZTI-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methoxy]isoindole-1,3-dione Chemical compound ClC1=CC=CC(Cl)=C1CON1C(=O)C2=CC=CC=C2C1=O QVMAVYVJYYXZTI-UHFFFAOYSA-N 0.000 description 1
- GIRZROTWZXVXPX-UHFFFAOYSA-N 2-[(2-chlorophenyl)methoxy]isoindole-1,3-dione Chemical compound ClC1=CC=CC=C1CON1C(=O)C2=CC=CC=C2C1=O GIRZROTWZXVXPX-UHFFFAOYSA-N 0.000 description 1
- HAGLBGMDUNPPEY-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methoxy]isoindole-1,3-dione Chemical compound C1=C(OC)C(OC)=CC=C1CON1C(=O)C2=CC=CC=C2C1=O HAGLBGMDUNPPEY-UHFFFAOYSA-N 0.000 description 1
- UCIAVHKXNQUJSE-UHFFFAOYSA-N 2-[(3,5-dichloro-4-methoxyphenyl)methoxy]isoindole-1,3-dione Chemical compound COC1=C(C=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=C1Cl)Cl UCIAVHKXNQUJSE-UHFFFAOYSA-N 0.000 description 1
- FJGLZNGMUGFYKW-UHFFFAOYSA-N 2-[(3-hydroxy-4-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound OC=1C=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=CC1[N+](=O)[O-] FJGLZNGMUGFYKW-UHFFFAOYSA-N 0.000 description 1
- MXLWOFFKIKAHTG-UHFFFAOYSA-N 2-[(3-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC(CON2C(C3=CC=CC=C3C2=O)=O)=C1 MXLWOFFKIKAHTG-UHFFFAOYSA-N 0.000 description 1
- GYNIVHPAPORJAL-UHFFFAOYSA-N 2-[(4-bromo-3-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound [N+](=O)([O-])C=1C=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=CC1Br GYNIVHPAPORJAL-UHFFFAOYSA-N 0.000 description 1
- DWVJTIVMISRPNK-UHFFFAOYSA-N 2-[(4-chlorophenyl)methoxy]isoindole-1,3-dione Chemical compound C1=CC(Cl)=CC=C1CON1C(=O)C2=CC=CC=C2C1=O DWVJTIVMISRPNK-UHFFFAOYSA-N 0.000 description 1
- SOFAQXZWOPUOLU-UHFFFAOYSA-N 2-[(4-hydroxy-3-methoxy-5-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound [N+](=O)([O-])C=1C=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=C(C1O)OC SOFAQXZWOPUOLU-UHFFFAOYSA-N 0.000 description 1
- AQJSPPKBAUPPGK-UHFFFAOYSA-N 2-[(4-hydroxy-3-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound [N+](=O)([O-])C=1C=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=CC1O AQJSPPKBAUPPGK-UHFFFAOYSA-N 0.000 description 1
- ZRWGEDROPYBYNC-UHFFFAOYSA-N 2-[(4-methoxy-3-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound [N+](=O)([O-])C=1C=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=CC1OC ZRWGEDROPYBYNC-UHFFFAOYSA-N 0.000 description 1
- HKVUKOYOPFEIBG-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methoxy]isoindole-1,3-dione Chemical compound C1=CC(OC)=CC=C1CON1C(=O)C2=CC=CC=C2C1=O HKVUKOYOPFEIBG-UHFFFAOYSA-N 0.000 description 1
- NHHXHECFCOJBLM-UHFFFAOYSA-N 2-[(4-methylphenyl)methoxy]isoindole-1,3-dione Chemical compound C1=CC(C)=CC=C1CON1C(=O)C2=CC=CC=C2C1=O NHHXHECFCOJBLM-UHFFFAOYSA-N 0.000 description 1
- DLKDEVCJRCPTLN-UHFFFAOYSA-N 2-butylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC)C(=O)C2=C1 DLKDEVCJRCPTLN-UHFFFAOYSA-N 0.000 description 1
- SJKISZSZWWOLCF-UHFFFAOYSA-N 2-ethoxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OCC)C(=O)C2=C1 SJKISZSZWWOLCF-UHFFFAOYSA-N 0.000 description 1
- WWBGXGNUKICTSR-UHFFFAOYSA-N 2-hexadecoxyisoindole-1,3-dione Chemical compound C(CCCCCCCCCCCCCCC)ON1C(C=2C(C1=O)=CC=CC2)=O WWBGXGNUKICTSR-UHFFFAOYSA-N 0.000 description 1
- VNEXAHNNMMMMON-UHFFFAOYSA-N 2-hexoxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OCCCCCC)C(=O)C2=C1 VNEXAHNNMMMMON-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- VTULOVFSIMMKKO-UHFFFAOYSA-N 2-methoxyisoindole-1,3-dione Chemical group C1=CC=C2C(=O)N(OC)C(=O)C2=C1 VTULOVFSIMMKKO-UHFFFAOYSA-N 0.000 description 1
- MFUPLJQNEXUUDW-UHFFFAOYSA-N 2-phenylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 MFUPLJQNEXUUDW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XMHFPYYNEAESCQ-UHFFFAOYSA-N 3-(aminooxymethyl)-N,N-diethyl-4-hydroxybenzamide Chemical compound C(C)N(C(C1=CC(=C(C=C1)O)CON)=O)CC XMHFPYYNEAESCQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- JHBUKXAVIKDFRP-UHFFFAOYSA-N 4-(1-aminooxyethyl)-2-nitrophenol Chemical compound [N+](=O)([O-])C=1C=C(C=CC1O)C(C)ON JHBUKXAVIKDFRP-UHFFFAOYSA-N 0.000 description 1
- ZZOVZWAVKJUBQQ-UHFFFAOYSA-N 4-(aminooxymethyl)-2-methoxy-6-nitrophenol Chemical compound [N+](=O)([O-])C=1C=C(CON)C=C(C1O)OC ZZOVZWAVKJUBQQ-UHFFFAOYSA-N 0.000 description 1
- PITNDATVERTKEN-UHFFFAOYSA-N 4-(aminooxymethyl)-2-nitrophenol Chemical compound NOCC1=CC=C(O)C([N+]([O-])=O)=C1 PITNDATVERTKEN-UHFFFAOYSA-N 0.000 description 1
- IXCHMZCDWDNGDW-UHFFFAOYSA-N 4-(aminooxymethyl)-2-nitrophenol hydrochloride Chemical compound Cl.[N+](=O)([O-])C=1C=C(CON)C=CC1O IXCHMZCDWDNGDW-UHFFFAOYSA-N 0.000 description 1
- TWUPNADZLRGOEH-UHFFFAOYSA-N 4-[(4-nitrophenyl)methoxy]isoindole-1,3-dione Chemical compound [N+](=O)([O-])C1=CC=C(COC2=C3C(C(=O)NC3=O)=CC=C2)C=C1 TWUPNADZLRGOEH-UHFFFAOYSA-N 0.000 description 1
- VWJGCEMQLKAWQH-UHFFFAOYSA-N 5-(aminooxymethyl)-2-nitrophenol Chemical compound NOCC1=CC=C([N+]([O-])=O)C(O)=C1 VWJGCEMQLKAWQH-UHFFFAOYSA-N 0.000 description 1
- ZSSBZAXWOWSEEH-UHFFFAOYSA-N 5-(aminooxymethyl)-2-nitrophenol;hydrochloride Chemical compound Cl.NOCC1=CC=C([N+]([O-])=O)C(O)=C1 ZSSBZAXWOWSEEH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000766026 Coregonus nasus Species 0.000 description 1
- WJAJPNHVVFWKKL-UHFFFAOYSA-N Methoxamine Chemical compound COC1=CC=C(OC)C(C(O)C(C)N)=C1 WJAJPNHVVFWKKL-UHFFFAOYSA-N 0.000 description 1
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 1
- RZINCIDRGNGHEK-UHFFFAOYSA-N O-[(3,5-dimethoxy-4-octoxyphenyl)methyl]hydroxylamine Chemical compound C(CCCCCCC)OC1=C(C=C(CON)C=C1OC)OC RZINCIDRGNGHEK-UHFFFAOYSA-N 0.000 description 1
- BTUNPCPDEALVAF-UHFFFAOYSA-N O-[(4-bromo-3-nitrophenyl)methyl]hydroxylamine Chemical compound [N+](=O)([O-])C=1C=C(CON)C=CC1Br BTUNPCPDEALVAF-UHFFFAOYSA-N 0.000 description 1
- JXVSVBKSYWLVTN-UHFFFAOYSA-N O-[(4-bromo-3-nitrophenyl)methyl]hydroxylamine hydrochloride Chemical compound Cl.[N+](=O)([O-])C=1C=C(CON)C=CC1Br JXVSVBKSYWLVTN-UHFFFAOYSA-N 0.000 description 1
- LNMMKKFTJLVODE-UHFFFAOYSA-N O-[(4-chloro-3-nitrophenyl)methyl]hydroxylamine hydrochloride Chemical compound Cl.[N+](=O)([O-])C=1C=C(CON)C=CC1Cl LNMMKKFTJLVODE-UHFFFAOYSA-N 0.000 description 1
- YXNXTRIEURQEFY-UHFFFAOYSA-N O-[(4-methoxy-3-nitrophenyl)methyl]hydroxylamine hydrochloride Chemical compound Cl.[N+](=O)([O-])C=1C=C(CON)C=CC1OC YXNXTRIEURQEFY-UHFFFAOYSA-N 0.000 description 1
- LSVQFKHQGBSJJB-UHFFFAOYSA-N O-[1-(3-nitrophenyl)ethyl]hydroxylamine Chemical compound [N+](=O)([O-])C=1C=C(C=CC1)C(C)ON LSVQFKHQGBSJJB-UHFFFAOYSA-N 0.000 description 1
- KFNDQQOROASPIO-UHFFFAOYSA-N O-hexadecylhydroxylamine hydrochloride Chemical compound Cl.C(CCCCCCCCCCCCCCC)ON KFNDQQOROASPIO-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- BHZVPXMDQWVLSQ-UHFFFAOYSA-N amino benzoate;hydrochloride Chemical compound Cl.NOC(=O)C1=CC=CC=C1 BHZVPXMDQWVLSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- LXTKCTMGEWVPTB-UHFFFAOYSA-N butylazanium;acetate Chemical compound CC(O)=O.CCCCN LXTKCTMGEWVPTB-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OBBCREYLPHMEEX-UHFFFAOYSA-N ethyl n-phenylmethoxycarbamate Chemical compound CCOC(=O)NOCC1=CC=CC=C1 OBBCREYLPHMEEX-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- DHEZQYZJFCIQQA-UHFFFAOYSA-N hydron;o-[(4-methoxyphenyl)methyl]hydroxylamine;chloride Chemical compound Cl.COC1=CC=C(CON)C=C1 DHEZQYZJFCIQQA-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- SLDJRAHLLZLUNE-UHFFFAOYSA-N methyl 3-(aminooxymethyl)-4,5-dihydroxybenzoate Chemical compound OC1=C(CON)C=C(C=C1O)C(=O)OC SLDJRAHLLZLUNE-UHFFFAOYSA-N 0.000 description 1
- TZAPXTYBMQBCIN-UHFFFAOYSA-N methyl 3-[(1,3-dioxoisoindol-2-yl)oxymethyl]-4,5-dihydroxybenzoate Chemical compound OC1=C(CON2C(C=3C(C2=O)=CC=CC3)=O)C=C(C=C1O)C(=O)OC TZAPXTYBMQBCIN-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940072395 n-butylphthalimide Drugs 0.000 description 1
- YGAWPVSHKADCLL-UHFFFAOYSA-N o-(1,3-benzothiazol-2-ylmethyl)hydroxylamine Chemical compound C1=CC=C2SC(CON)=NC2=C1 YGAWPVSHKADCLL-UHFFFAOYSA-N 0.000 description 1
- DMAJXJBCAAMVCT-UHFFFAOYSA-N o-(1h-imidazol-5-ylmethyl)hydroxylamine Chemical compound NOCC1=CNC=N1 DMAJXJBCAAMVCT-UHFFFAOYSA-N 0.000 description 1
- PMPPBLLDPIXDRE-UHFFFAOYSA-N o-(pyridin-2-ylmethyl)hydroxylamine Chemical compound NOCC1=CC=CC=N1 PMPPBLLDPIXDRE-UHFFFAOYSA-N 0.000 description 1
- QFRHQZLHZLSOHJ-UHFFFAOYSA-N o-(pyridin-2-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=CC=N1 QFRHQZLHZLSOHJ-UHFFFAOYSA-N 0.000 description 1
- TVPSRTVMZGECAT-UHFFFAOYSA-N o-(pyridin-3-ylmethyl)hydroxylamine Chemical compound NOCC1=CC=CN=C1 TVPSRTVMZGECAT-UHFFFAOYSA-N 0.000 description 1
- GGJNRSIKHOXICL-UHFFFAOYSA-N o-(pyridin-4-ylmethyl)hydroxylamine Chemical compound NOCC1=CC=NC=C1 GGJNRSIKHOXICL-UHFFFAOYSA-N 0.000 description 1
- INOCPWZDQJBNMJ-UHFFFAOYSA-N o-(pyridin-4-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=NC=C1 INOCPWZDQJBNMJ-UHFFFAOYSA-N 0.000 description 1
- FWOFPXVVUMLSCV-UHFFFAOYSA-N o-[(1-methylbenzimidazol-2-yl)methyl]hydroxylamine Chemical compound C1=CC=C2N(C)C(CON)=NC2=C1 FWOFPXVVUMLSCV-UHFFFAOYSA-N 0.000 description 1
- ZZAXSKXALNKDRJ-UHFFFAOYSA-N o-[(2,6-dichlorophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=C(Cl)C=CC=C1Cl ZZAXSKXALNKDRJ-UHFFFAOYSA-N 0.000 description 1
- WJWMBNQCKBRAHA-UHFFFAOYSA-N o-[(2-chlorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=CC=C1Cl WJWMBNQCKBRAHA-UHFFFAOYSA-N 0.000 description 1
- XWKUZVURFYMSBF-UHFFFAOYSA-N o-[(3,4,5-trimethoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC(CON)=CC(OC)=C1OC XWKUZVURFYMSBF-UHFFFAOYSA-N 0.000 description 1
- WDIYOALRWSMTRN-UHFFFAOYSA-N o-[(3,4,5-trimethoxyphenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC(CON)=CC(OC)=C1OC WDIYOALRWSMTRN-UHFFFAOYSA-N 0.000 description 1
- OVMBDDNTFJQHST-UHFFFAOYSA-N o-[(3,4-dichlorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=C(Cl)C(Cl)=C1 OVMBDDNTFJQHST-UHFFFAOYSA-N 0.000 description 1
- LEUZSWJUEHCRFM-UHFFFAOYSA-N o-[(3,4-dichlorophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=C(Cl)C(Cl)=C1 LEUZSWJUEHCRFM-UHFFFAOYSA-N 0.000 description 1
- SUZMAAZWMHDSHJ-UHFFFAOYSA-N o-[(3,4-dimethoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC=C(CON)C=C1OC SUZMAAZWMHDSHJ-UHFFFAOYSA-N 0.000 description 1
- KBXVIQKLRHKPEJ-UHFFFAOYSA-N o-[(3-methoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC=CC(CON)=C1 KBXVIQKLRHKPEJ-UHFFFAOYSA-N 0.000 description 1
- DNGAZMVOQCQJIG-UHFFFAOYSA-N o-[(3-methoxyphenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC=CC(CON)=C1 DNGAZMVOQCQJIG-UHFFFAOYSA-N 0.000 description 1
- JTKYPOYHPKGJGX-UHFFFAOYSA-N o-[(3-nitrophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=CC([N+]([O-])=O)=C1 JTKYPOYHPKGJGX-UHFFFAOYSA-N 0.000 description 1
- VHTDJDWKRJRXDM-UHFFFAOYSA-N o-[(3-nitrophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=CC([N+]([O-])=O)=C1 VHTDJDWKRJRXDM-UHFFFAOYSA-N 0.000 description 1
- YBNXWPOMGHUNKW-UHFFFAOYSA-N o-[(4-chloro-3-nitrophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=C(Cl)C([N+]([O-])=O)=C1 YBNXWPOMGHUNKW-UHFFFAOYSA-N 0.000 description 1
- GONDHKVGJCQJPR-UHFFFAOYSA-N o-[(4-chlorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=C(Cl)C=C1 GONDHKVGJCQJPR-UHFFFAOYSA-N 0.000 description 1
- VIFDVZZLHVXUHV-UHFFFAOYSA-N o-[(4-chlorophenyl)methyl]hydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=C(Cl)C=C1 VIFDVZZLHVXUHV-UHFFFAOYSA-N 0.000 description 1
- MVSMBIBGGPSEHQ-UHFFFAOYSA-N o-[(4-methoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC=C(CON)C=C1 MVSMBIBGGPSEHQ-UHFFFAOYSA-N 0.000 description 1
- MLWXTMVARHZBPA-UHFFFAOYSA-N o-[(4-methylphenyl)methyl]hydroxylamine Chemical compound CC1=CC=C(CON)C=C1 MLWXTMVARHZBPA-UHFFFAOYSA-N 0.000 description 1
- NBWBUEQJIPSFEX-UHFFFAOYSA-N o-[(4-methylphenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.CC1=CC=C(CON)C=C1 NBWBUEQJIPSFEX-UHFFFAOYSA-N 0.000 description 1
- LFEDBDWFFNNYNT-UHFFFAOYSA-N o-hexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCON LFEDBDWFFNNYNT-UHFFFAOYSA-N 0.000 description 1
- AIPBDRLFQKUETL-UHFFFAOYSA-N o-hexylhydroxylamine Chemical compound CCCCCCON AIPBDRLFQKUETL-UHFFFAOYSA-N 0.000 description 1
- RUMYSLNKNKBRJJ-UHFFFAOYSA-N o-hexylhydroxylamine;hydrochloride Chemical compound Cl.CCCCCCON RUMYSLNKNKBRJJ-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001155 HU162578B (enrdf_load_stackoverflow) | 1971-02-15 | 1971-02-15 | |
| HUGO001155 | 1971-02-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142027B true DK142027B (da) | 1980-08-11 |
| DK142027C DK142027C (enrdf_load_stackoverflow) | 1981-02-16 |
Family
ID=10996690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK66872A DK142027B (da) | 1971-02-15 | 1972-02-14 | Fremgangsmåde til fremstilling af substituerede methoxyaminer. |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT316511B (enrdf_load_stackoverflow) |
| CA (1) | CA989394A (enrdf_load_stackoverflow) |
| CH (1) | CH566961A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2206890A1 (enrdf_load_stackoverflow) |
| DK (1) | DK142027B (enrdf_load_stackoverflow) |
| FR (1) | FR2131350A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1331203A (enrdf_load_stackoverflow) |
| HU (1) | HU162578B (enrdf_load_stackoverflow) |
| NL (1) | NL7201784A (enrdf_load_stackoverflow) |
| SE (1) | SE387936B (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2651083A1 (de) * | 1976-11-09 | 1978-05-18 | Hoechst Ag | Neue o-alkylierte hydroxylamine, verfahren zu ihrer herstellung und ihre verwendung |
| DE3615473A1 (de) * | 1986-05-07 | 1987-11-12 | Basf Ag | Verfahren zur herstellung von o-substituierten hydroxylaminen |
| AUPM910994A0 (en) * | 1994-10-28 | 1994-11-24 | Commonwealth Scientific And Industrial Research Organisation | Bisallyloxyimides |
| AU705642B2 (en) * | 1994-10-28 | 1999-05-27 | Commonwealth Scientific And Industrial Research Organisation | Bisallyloxyimides |
| DE10301519A1 (de) | 2003-01-17 | 2004-07-29 | Bayer Cropscience Ag | 9-Ketospinosyn-Derivate |
| CA2932121A1 (en) * | 2007-11-30 | 2009-06-11 | Newlink Genetics Corporation | Ido inhibitors |
-
1971
- 1971-02-15 HU HUGO001155 patent/HU162578B/hu unknown
-
1972
- 1972-02-07 GB GB553172A patent/GB1331203A/en not_active Expired
- 1972-02-10 CA CA134,406A patent/CA989394A/en not_active Expired
- 1972-02-11 NL NL7201784A patent/NL7201784A/xx not_active Application Discontinuation
- 1972-02-14 DK DK66872A patent/DK142027B/da unknown
- 1972-02-14 DE DE19722206890 patent/DE2206890A1/de active Pending
- 1972-02-14 SE SE173272A patent/SE387936B/xx unknown
- 1972-02-15 AT AT120172A patent/AT316511B/de not_active IP Right Cessation
- 1972-02-15 FR FR7204947A patent/FR2131350A5/fr not_active Expired
- 1972-02-15 CH CH214772A patent/CH566961A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1331203A (en) | 1973-09-26 |
| SE387936B (sv) | 1976-09-20 |
| NL7201784A (enrdf_load_stackoverflow) | 1972-08-17 |
| DK142027C (enrdf_load_stackoverflow) | 1981-02-16 |
| AT316511B (de) | 1974-07-10 |
| FR2131350A5 (enrdf_load_stackoverflow) | 1972-11-10 |
| DE2206890A1 (de) | 1972-08-31 |
| HU162578B (enrdf_load_stackoverflow) | 1973-03-28 |
| CH566961A5 (enrdf_load_stackoverflow) | 1975-09-30 |
| CA989394A (en) | 1976-05-18 |
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