DE1815802A1 - Verfahren zur Herstellung von substituierten Phenylessigsaeuren - Google Patents
Verfahren zur Herstellung von substituierten PhenylessigsaeurenInfo
- Publication number
- DE1815802A1 DE1815802A1 DE19681815802 DE1815802A DE1815802A1 DE 1815802 A1 DE1815802 A1 DE 1815802A1 DE 19681815802 DE19681815802 DE 19681815802 DE 1815802 A DE1815802 A DE 1815802A DE 1815802 A1 DE1815802 A1 DE 1815802A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- general formula
- substituted
- phenyl
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 16
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- XFBFAOFHQQXDCX-UHFFFAOYSA-N 2-(2-anilinophenyl)-2-oxoacetic acid Chemical compound N(C1=CC=CC=C1)C1=C(C=CC=C1)C(C(=O)O)=O XFBFAOFHQQXDCX-UHFFFAOYSA-N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 229960003424 phenylacetic acid Drugs 0.000 claims description 4
- 239000003279 phenylacetic acid Substances 0.000 claims description 4
- 238000006722 reduction reaction Methods 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
- 239000000243 solution Substances 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 14
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy Chemical group 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 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 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- SQIUEWNROMQRQY-UHFFFAOYSA-N 2,6-dimethyl-n-phenylaniline Chemical group CC1=CC=CC(C)=C1NC1=CC=CC=C1 SQIUEWNROMQRQY-UHFFFAOYSA-N 0.000 description 3
- XIUHOHOPFVHIEV-UHFFFAOYSA-N 2-[2-(2,6-dimethylanilino)phenyl]-2-oxoacetic acid Chemical compound CC1=C(NC2=C(C=CC=C2)C(C(=O)O)=O)C(=CC=C1)C XIUHOHOPFVHIEV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- SLPAPGNFCSVQKP-UHFFFAOYSA-N 2,6-dichloro-3-methyl-n-phenylaniline Chemical compound CC1=CC=C(Cl)C(NC=2C=CC=CC=2)=C1Cl SLPAPGNFCSVQKP-UHFFFAOYSA-N 0.000 description 2
- HDUUZPLYVVQTKN-UHFFFAOYSA-N 2,6-dichloro-n-phenylaniline Chemical compound ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 HDUUZPLYVVQTKN-UHFFFAOYSA-N 0.000 description 2
- TXARYTJORYGQKX-UHFFFAOYSA-N 2,6-dimethyl-n-(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1NC1=C(C)C=CC=C1C TXARYTJORYGQKX-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- FAFKIFYBYASEDL-UHFFFAOYSA-N 2-(2,6-dichloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl FAFKIFYBYASEDL-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- HOVGGLRIZGQIJM-UHFFFAOYSA-N 2-(4-methoxy-3-methylanilino)benzoic acid Chemical compound C1=C(C)C(OC)=CC=C1NC1=CC=CC=C1C(O)=O HOVGGLRIZGQIJM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ICJTVRXTYOYEOT-UHFFFAOYSA-N 2-[2-(2,6-dimethylanilino)phenyl]acetic acid Chemical compound CC1=CC=CC(C)=C1NC1=CC=CC=C1CC(O)=O ICJTVRXTYOYEOT-UHFFFAOYSA-N 0.000 description 2
- AHXBTNJVGFKVSX-UHFFFAOYSA-N 2-[2-(3-chloro-2-methylanilino)phenyl]-2-oxoacetic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(=O)C(O)=O AHXBTNJVGFKVSX-UHFFFAOYSA-N 0.000 description 2
- NXHYVXRWKQWGCL-UHFFFAOYSA-N 2-chloro-6-methyl-n-phenylaniline Chemical compound CC1=CC=CC(Cl)=C1NC1=CC=CC=C1 NXHYVXRWKQWGCL-UHFFFAOYSA-N 0.000 description 2
- 241001203928 Aethes Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- DWVWVSLAIJHBBG-UHFFFAOYSA-N n-(2,6-dichlorophenyl)acetamide Chemical compound CC(=O)NC1=C(Cl)C=CC=C1Cl DWVWVSLAIJHBBG-UHFFFAOYSA-N 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000003349 semicarbazides Chemical class 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MGEGDVKBXGZTRM-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)indole-2,3-dione Chemical compound ClC1=CC=CC(Cl)=C1N1C2=CC=CC=C2C(=O)C1=O MGEGDVKBXGZTRM-UHFFFAOYSA-N 0.000 description 1
- NMZDCIXVKOQWIW-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)indole-2,3-dione Chemical compound CC1=C(Cl)C=CC=C1N1C2=CC=CC=C2C(=O)C1=O NMZDCIXVKOQWIW-UHFFFAOYSA-N 0.000 description 1
- MBGSBDUEVSDONF-UHFFFAOYSA-N 1-(4-methoxy-3-methylphenyl)indole-2,3-dione Chemical compound COC1=CC=C(C=C1C)N1C(C(C2=CC=CC=C12)=O)=O MBGSBDUEVSDONF-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- ZHYOSPVQRODITN-UHFFFAOYSA-N 1-ethylpiperidine morpholine Chemical compound C1COCCN1.CCN1CCCCC1 ZHYOSPVQRODITN-UHFFFAOYSA-N 0.000 description 1
- OWPNVXATCSXTBK-UHFFFAOYSA-N 1-phenyl-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C1=CC=CC=C1 OWPNVXATCSXTBK-UHFFFAOYSA-N 0.000 description 1
- QTYVNNSDUDVLFJ-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylanilino)benzoic acid Chemical compound CC1=C(Cl)C=CC(NC=2C(=CC=CC=2)C(O)=O)=C1Cl QTYVNNSDUDVLFJ-UHFFFAOYSA-N 0.000 description 1
- JOXPQVQKTURDSS-UHFFFAOYSA-N 2-(2,6-dimethylanilino)-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1NC1=C(C)C=CC=C1C JOXPQVQKTURDSS-UHFFFAOYSA-N 0.000 description 1
- ZKYWDEUSHBRHBI-UHFFFAOYSA-N 2-(2,6-dimethylanilino)benzoic acid Chemical compound CC1=CC=CC(C)=C1NC1=CC=CC=C1C(O)=O ZKYWDEUSHBRHBI-UHFFFAOYSA-N 0.000 description 1
- NJFCAWNKWPIBAG-UHFFFAOYSA-N 2-(2-anilinophenyl)acetic acid Chemical class OC(=O)CC1=CC=CC=C1NC1=CC=CC=C1 NJFCAWNKWPIBAG-UHFFFAOYSA-N 0.000 description 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- CNQCAFDKWBMIJV-UHFFFAOYSA-N 2-[2-(2,4-dichloro-3-methylanilino)phenyl]acetic acid Chemical compound CC1=C(Cl)C=CC(NC=2C(=CC=CC=2)CC(O)=O)=C1Cl CNQCAFDKWBMIJV-UHFFFAOYSA-N 0.000 description 1
- MWPZLYLEVLUDNL-UHFFFAOYSA-N 2-[2-(3-chloro-2-methylanilino)phenyl]acetic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1CC(O)=O MWPZLYLEVLUDNL-UHFFFAOYSA-N 0.000 description 1
- VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 1
- GRIXINIGTYIHSN-UHFFFAOYSA-N 2-chloro-n,n-diphenylacetamide Chemical class C=1C=CC=CC=1N(C(=O)CCl)C1=CC=CC=C1 GRIXINIGTYIHSN-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- PAGQEMVOSGYMNU-UHFFFAOYSA-N 2-methoxy-5-methyl-N-phenylaniline Chemical compound C1(=CC=CC=C1)NC1=C(C=CC(=C1)C)OC PAGQEMVOSGYMNU-UHFFFAOYSA-N 0.000 description 1
- BCLQROPHEBEQCM-UHFFFAOYSA-N 3,5-dichloro-4-methoxy-N-[(4-methoxyphenyl)methyl]aniline Chemical compound C(C1=CC=C(C=C1)OC)NC1=CC(=C(OC)C(=C1)Cl)Cl BCLQROPHEBEQCM-UHFFFAOYSA-N 0.000 description 1
- VAJCSPZKMVQIAP-UHFFFAOYSA-N 5-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1 VAJCSPZKMVQIAP-UHFFFAOYSA-N 0.000 description 1
- YRLCJTLJODVGRC-UHFFFAOYSA-N COC1=CC=C(C=C1C)NC1=C(C=CC=C1)CC(=O)O Chemical compound COC1=CC=C(C=C1C)NC1=C(C=CC=C1)CC(=O)O YRLCJTLJODVGRC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 1
- DQYPHQHFXVXYRN-UHFFFAOYSA-N N(C=1C(=CC=CC=1C)C)C1=C(C=CC=C1CC(=O)O)C Chemical compound N(C=1C(=CC=CC=1C)C)C1=C(C=CC=C1CC(=O)O)C DQYPHQHFXVXYRN-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1789367A CH485667A (de) | 1967-12-20 | 1967-12-20 | Verfahren zur Herstellung von substituierten Phenylessigsäuren |
| CH1789267A CH487840A (de) | 1967-12-20 | 1967-12-20 | Verfahren zur Herstellung von substituierten Phenylessigsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1815802A1 true DE1815802A1 (de) | 1969-07-10 |
Family
ID=25720227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681815802 Pending DE1815802A1 (de) | 1967-12-20 | 1968-12-19 | Verfahren zur Herstellung von substituierten Phenylessigsaeuren |
Country Status (16)
| Country | Link |
|---|---|
| JP (4) | JPS5220469B1 (en, 2012) |
| AT (1) | AT284823B (en, 2012) |
| BE (1) | BE725793A (en, 2012) |
| CS (2) | CS151495B2 (en, 2012) |
| DE (1) | DE1815802A1 (en, 2012) |
| DK (1) | DK125461B (en, 2012) |
| ES (1) | ES361666A1 (en, 2012) |
| FI (1) | FI49600C (en, 2012) |
| FR (1) | FR1595382A (en, 2012) |
| GB (1) | GB1257190A (en, 2012) |
| IE (1) | IE32591B1 (en, 2012) |
| IL (1) | IL31296A (en, 2012) |
| NL (1) | NL6817965A (en, 2012) |
| NO (1) | NO125724B (en, 2012) |
| SE (1) | SE366296B (en, 2012) |
| YU (1) | YU32986B (en, 2012) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166128A (en) * | 1977-06-23 | 1979-08-28 | Asahi Kasei Kogyo Kabushiki Kaisha | Substituted phenylglycolic acid and its pharmaceutically acceptable esters and salts, and processes for preparing the same |
| FR2499980A1 (fr) * | 1981-02-16 | 1982-08-20 | Ciba Geigy Ag | Le (o-(2,6-dichloranilino))-phenylacetate de n-methyl-d-glucammonium, son obtention et les preparations pharmaceutiques le contenant |
| FR2500751A1 (fr) * | 1981-02-24 | 1982-09-03 | Ciba Geigy Ag | Compositions pharmaceutiques anti-inflammatoires topiques a base de sels d'acides carboxyliques, nouveaux sels d'acides carboxyliques et leur preparation |
| EP0122219A3 (en) * | 1983-01-12 | 1985-05-08 | Ciba-Geigy Ag | Substituted carboxylic-acid resins, process for their manafacture, use thereof and pharmaceutical compositions containing these resins |
| US5403958A (en) * | 1990-09-04 | 1995-04-04 | Hitachi Chemical Co., Ltd. | Electrophotographic member |
| WO2006058592A1 (en) | 2004-12-01 | 2006-06-08 | Merck Patent Gmbh | Novel specific caspase-10 inhibitors |
| EP2756843A2 (en) | 2006-07-25 | 2014-07-23 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate |
| US11834388B2 (en) | 2022-02-25 | 2023-12-05 | Fudan University | Continuous-flow preparation method of diclofenac sodium |
| US11905229B2 (en) | 2022-02-25 | 2024-02-20 | Fudan University | Method for synthesizing diclofenac sodium |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1112024B (it) * | 1979-02-23 | 1986-01-13 | Alcar Srl | Processo per la preparazione dell'acido o.(2,6-dicloroanilino)-fenilacetico |
| JPS6341143U (en, 2012) * | 1986-09-02 | 1988-03-17 | ||
| US6355680B1 (en) * | 1996-02-20 | 2002-03-12 | Exocell, Inc. | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
| AR061623A1 (es) | 2006-06-26 | 2008-09-10 | Novartis Ag | Derivados de acido fenilacetico |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5220469A (en) * | 1975-08-08 | 1977-02-16 | Mitsui Toatsu Chem Inc | Method for grading granule |
| JPS5851859B2 (ja) * | 1978-08-11 | 1983-11-18 | 株式会社日立製作所 | 帳票送り出し装置 |
-
1968
- 1968-12-13 NL NL6817965A patent/NL6817965A/xx unknown
- 1968-12-13 NO NO5013/68A patent/NO125724B/no unknown
- 1968-12-13 SE SE17151/68A patent/SE366296B/xx unknown
- 1968-12-13 FI FI683591A patent/FI49600C/fi active
- 1968-12-13 DK DK612768AA patent/DK125461B/da not_active IP Right Cessation
- 1968-12-17 YU YU2983/68A patent/YU32986B/xx unknown
- 1968-12-19 IE IE1536/68A patent/IE32591B1/xx unknown
- 1968-12-19 CS CS8634A patent/CS151495B2/cs unknown
- 1968-12-19 DE DE19681815802 patent/DE1815802A1/de active Pending
- 1968-12-19 JP JP43092731A patent/JPS5220469B1/ja active Pending
- 1968-12-19 IL IL31296A patent/IL31296A/en unknown
- 1968-12-19 ES ES361666A patent/ES361666A1/es not_active Expired
- 1968-12-19 GB GB1257190D patent/GB1257190A/en not_active Expired
- 1968-12-19 FR FR1595382D patent/FR1595382A/fr not_active Expired
- 1968-12-19 AT AT1236868A patent/AT284823B/de not_active IP Right Cessation
- 1968-12-19 CS CS5436*[A patent/CS151496B2/cs unknown
- 1968-12-20 BE BE725793D patent/BE725793A/xx not_active IP Right Cessation
-
1978
- 1978-06-07 JP JP6871878A patent/JPS5526131B1/ja active Pending
- 1978-10-31 JP JP13440778A patent/JPS5635664B1/ja active Pending
-
1979
- 1979-05-02 JP JP5465379A patent/JPS5526132B1/ja active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166128A (en) * | 1977-06-23 | 1979-08-28 | Asahi Kasei Kogyo Kabushiki Kaisha | Substituted phenylglycolic acid and its pharmaceutically acceptable esters and salts, and processes for preparing the same |
| FR2499980A1 (fr) * | 1981-02-16 | 1982-08-20 | Ciba Geigy Ag | Le (o-(2,6-dichloranilino))-phenylacetate de n-methyl-d-glucammonium, son obtention et les preparations pharmaceutiques le contenant |
| WO1982002889A1 (fr) * | 1981-02-16 | 1982-09-02 | Geigy Ag Ciba | Sels d'ammonium d'un acide carbonique substitue, leur procede de preparation, utilisation et preparation medicamenteuses les renfermant |
| FR2500751A1 (fr) * | 1981-02-24 | 1982-09-03 | Ciba Geigy Ag | Compositions pharmaceutiques anti-inflammatoires topiques a base de sels d'acides carboxyliques, nouveaux sels d'acides carboxyliques et leur preparation |
| EP0122219A3 (en) * | 1983-01-12 | 1985-05-08 | Ciba-Geigy Ag | Substituted carboxylic-acid resins, process for their manafacture, use thereof and pharmaceutical compositions containing these resins |
| AT391467B (de) * | 1983-01-12 | 1990-10-10 | Ciba Geigy Ag | Verfahren zur herstellung eines beladenen ionenaustauscherharzes sowie die herstellung pharmazeutischer praeparate hiemit |
| US5403958A (en) * | 1990-09-04 | 1995-04-04 | Hitachi Chemical Co., Ltd. | Electrophotographic member |
| WO2006058592A1 (en) | 2004-12-01 | 2006-06-08 | Merck Patent Gmbh | Novel specific caspase-10 inhibitors |
| EP2756843A2 (en) | 2006-07-25 | 2014-07-23 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate |
| US11834388B2 (en) | 2022-02-25 | 2023-12-05 | Fudan University | Continuous-flow preparation method of diclofenac sodium |
| US11905229B2 (en) | 2022-02-25 | 2024-02-20 | Fudan University | Method for synthesizing diclofenac sodium |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6817965A (en, 2012) | 1969-06-24 |
| JPS5526132B1 (en, 2012) | 1980-07-11 |
| GB1257190A (en, 2012) | 1971-12-15 |
| NO125724B (en, 2012) | 1972-10-23 |
| FI49600C (fi) | 1975-08-11 |
| FI49600B (en, 2012) | 1975-04-30 |
| IE32591B1 (en) | 1973-09-19 |
| CS151495B2 (en, 2012) | 1973-10-19 |
| IL31296A (en) | 1972-06-28 |
| YU32986B (en) | 1975-12-31 |
| FR1595382A (en, 2012) | 1970-06-08 |
| DK125461B (da) | 1973-02-26 |
| ES361666A1 (es) | 1970-11-16 |
| BE725793A (en, 2012) | 1969-06-20 |
| CS151496B2 (en, 2012) | 1973-10-19 |
| JPS5635664B1 (en, 2012) | 1981-08-19 |
| AT284823B (de) | 1970-09-25 |
| JPS5526131B1 (en, 2012) | 1980-07-11 |
| YU298368A (en) | 1975-06-30 |
| IL31296A0 (en) | 1969-02-27 |
| JPS5220469B1 (en, 2012) | 1977-06-03 |
| IE32591L (en) | 1969-06-20 |
| SE366296B (en, 2012) | 1974-04-22 |
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