BE724727A - - Google Patents
Info
- Publication number
- BE724727A BE724727A BE724727DA BE724727A BE 724727 A BE724727 A BE 724727A BE 724727D A BE724727D A BE 724727DA BE 724727 A BE724727 A BE 724727A
- Authority
- BE
- Belgium
- Prior art keywords
- derivative
- indole
- formula
- carboxylic acid
- reacting
- Prior art date
Links
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 77
- -1 indole-2-carbonyl halide Chemical class 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 63
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical class OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 claims description 27
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 26
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical class C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 claims description 25
- RNAODKZCUVVPEN-UHFFFAOYSA-N 1h-indol-2-ylmethanamine Chemical class C1=CC=C2NC(CN)=CC2=C1 RNAODKZCUVVPEN-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000003638 chemical reducing agent Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 9
- LGROKZMEHJZWDU-UHFFFAOYSA-N n-amino-n-phenylnitramide Chemical class [O-][N+](=O)N(N)C1=CC=CC=C1 LGROKZMEHJZWDU-UHFFFAOYSA-N 0.000 claims description 8
- 239000012024 dehydrating agents Substances 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 230000002140 halogenating effect Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 3
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical group C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 6
- 150000008050 dialkyl sulfates Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 110
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 61
- 239000000203 mixture Substances 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 41
- 230000008018 melting Effects 0.000 description 41
- 239000000243 solution Substances 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000001914 filtration Methods 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- 239000002244 precipitate Substances 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 238000001816 cooling Methods 0.000 description 18
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 16
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 150000001557 benzodiazepines Chemical class 0.000 description 15
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 235000019253 formic acid Nutrition 0.000 description 12
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 10
- BMZNTPXQZKYUKD-UHFFFAOYSA-N 5-nitro-3-phenyl-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 BMZNTPXQZKYUKD-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 150000007524 organic acids Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 9
- 239000012188 paraffin wax Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 235000011118 potassium hydroxide Nutrition 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- CLRHEGMAWYPMJF-UHFFFAOYSA-N ethyl 2-oxo-3-phenylpropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=CC=C1 CLRHEGMAWYPMJF-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229940076788 pyruvate Drugs 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- NMTWMLNKZLCINX-UHFFFAOYSA-N 1-ethyl-5-nitro-3-phenylindole-2-carboxylic acid Chemical compound C(C)N1C(=C(C2=CC(=CC=C12)[N+](=O)[O-])C1=CC=CC=C1)C(=O)O NMTWMLNKZLCINX-UHFFFAOYSA-N 0.000 description 6
- YJZSZDLYSIYJDV-UHFFFAOYSA-N 1-methyl-5-nitro-3-phenylindole-2-carboxylic acid Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)C(C(O)=O)=C1C1=CC=CC=C1 YJZSZDLYSIYJDV-UHFFFAOYSA-N 0.000 description 6
- YPHLYLTWLDQJPX-UHFFFAOYSA-N 5-nitro-3-phenyl-1H-indole-2-carboxamide Chemical compound [N+](=O)([O-])C=1C=C2C(=C(NC2=CC1)C(=O)N)C1=CC=CC=C1 YPHLYLTWLDQJPX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- RWWDKSRRVDTYNM-UHFFFAOYSA-N ethyl 5-nitro-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 RWWDKSRRVDTYNM-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- FHGASLDDIOIKCP-UHFFFAOYSA-N 1-methyl-5-nitro-3-phenylindole-2-carbonitrile Chemical compound CN1C(=C(C2=CC(=CC=C12)[N+](=O)[O-])C1=CC=CC=C1)C#N FHGASLDDIOIKCP-UHFFFAOYSA-N 0.000 description 5
- ZOVSPAWAAGKIMQ-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-nitro-1H-indole-2-carboxylic acid Chemical compound FC1=C(C=CC=C1)C1=C(NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)O ZOVSPAWAAGKIMQ-UHFFFAOYSA-N 0.000 description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
- BQXZKLVLIANTAV-UHFFFAOYSA-N 7-nitro-3-phenyl-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=C([N+]([O-])=O)C=CC=C2C=1C1=CC=CC=C1 BQXZKLVLIANTAV-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- RLWCBNUYDMVYDZ-UHFFFAOYSA-N 1-methyl-5-nitro-3-phenylindole-2-carboxamide Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)C(C(N)=O)=C1C1=CC=CC=C1 RLWCBNUYDMVYDZ-UHFFFAOYSA-N 0.000 description 4
- AYTSDBGAHOKDHJ-UHFFFAOYSA-N 2-nitrobenzenediazonium Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]#N AYTSDBGAHOKDHJ-UHFFFAOYSA-N 0.000 description 4
- KAUUDUOWBCJTIQ-UHFFFAOYSA-N 3-(2-bromophenyl)-5-nitro-1H-indole-2-carboxylic acid Chemical compound BrC1=C(C=CC=C1)C1=C(NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)O KAUUDUOWBCJTIQ-UHFFFAOYSA-N 0.000 description 4
- BOBALZQTYSAHMC-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-5-nitroindole-2-carboxylic acid Chemical compound FC1=C(C=CC=C1)C1=C(N(C2=CC=C(C=C12)[N+](=O)[O-])C)C(=O)O BOBALZQTYSAHMC-UHFFFAOYSA-N 0.000 description 4
- YOFGRJCOOVQZKZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-nitro-1H-indole-2-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C1=C(NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)O YOFGRJCOOVQZKZ-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IXZWONRTTZLUPX-UHFFFAOYSA-N ClC1=C(C=CC=C1)C1=C(N(C2=CC=C(C=C12)[N+](=O)[O-])C)C(=O)O Chemical compound ClC1=C(C=CC=C1)C1=C(N(C2=CC=C(C=C12)[N+](=O)[O-])C)C(=O)O IXZWONRTTZLUPX-UHFFFAOYSA-N 0.000 description 4
- 238000007126 N-alkylation reaction Methods 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- JUBOEJUOHIMJKT-UHFFFAOYSA-N ethyl 2-[(4-nitrophenyl)hydrazinylidene]-3-phenylpropanoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1NN=C(C(=O)OCC)CC1=CC=CC=C1 JUBOEJUOHIMJKT-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KVDSMSTWFMXINV-UHFFFAOYSA-N (1-methyl-5-nitro-3-phenylindol-2-yl)methanamine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)C(CN)=C1C1=CC=CC=C1 KVDSMSTWFMXINV-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- FXQFLIXDJDMANZ-UHFFFAOYSA-N 5-nitro-3-phenyl-1-propylindole-2-carbonitrile Chemical compound C(CC)N1C(=C(C2=CC(=CC=C12)[N+](=O)[O-])C1=CC=CC=C1)C#N FXQFLIXDJDMANZ-UHFFFAOYSA-N 0.000 description 3
- CBURQRILDSBWCF-UHFFFAOYSA-N 5-nitro-3-phenyl-1-propylindole-2-carboxamide Chemical compound C(CC)N1C(=C(C2=CC(=CC=C12)[N+](=O)[O-])C1=CC=CC=C1)C(=O)N CBURQRILDSBWCF-UHFFFAOYSA-N 0.000 description 3
- DSWVTYMKIQJSLM-UHFFFAOYSA-N 5-nitro-3-phenyl-1h-indole-2-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(C#N)=C1C1=CC=CC=C1 DSWVTYMKIQJSLM-UHFFFAOYSA-N 0.000 description 3
- TURSLXNQZUMZQC-UHFFFAOYSA-N CC(C)(C)OC(C(NC(C1=C2)=CC=C2[N+]([O-])=O)=C1C1=CC=CC=C1)=O Chemical compound CC(C)(C)OC(C(NC(C1=C2)=CC=C2[N+]([O-])=O)=C1C1=CC=CC=C1)=O TURSLXNQZUMZQC-UHFFFAOYSA-N 0.000 description 3
- XDWQYMXQMNUWID-UHFFFAOYSA-N Ethyl 2-benzylacetoacetate Chemical compound CCOC(=O)C(C(C)=O)CC1=CC=CC=C1 XDWQYMXQMNUWID-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002841 Lewis acid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- KAOSFPBSWNREAY-UHFFFAOYSA-N methyl 2-oxo-3-phenylpropanoate Chemical compound COC(=O)C(=O)CC1=CC=CC=C1 KAOSFPBSWNREAY-UHFFFAOYSA-N 0.000 description 3
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- UGRGEXWAFJKDRD-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=C(NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)OCC Chemical compound ClC=1C=C(C=CC=1)C1=C(NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)OCC UGRGEXWAFJKDRD-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- RXGVJTWTLDFFHY-UHFFFAOYSA-N NCC=1N(C2=CC=C(C=C2C=1C1=C(C=CC=C1)F)[N+](=O)[O-])C Chemical compound NCC=1N(C2=CC=C(C=C2C=1C1=C(C=CC=C1)F)[N+](=O)[O-])C RXGVJTWTLDFFHY-UHFFFAOYSA-N 0.000 description 1
- PXWOTEKDLCKMHN-UHFFFAOYSA-N NCC=1N(C2=CC=C(C=C2C=1C1=CC=CC=C1)[N+](=O)[O-])CCC Chemical compound NCC=1N(C2=CC=C(C=C2C=1C1=CC=CC=C1)[N+](=O)[O-])CCC PXWOTEKDLCKMHN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- KIWZKBUUWJTGPP-UHFFFAOYSA-N [2-(methylamino)-5-nitrophenyl]-phenylmethanone Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 KIWZKBUUWJTGPP-UHFFFAOYSA-N 0.000 description 1
- UGJVZXBXVRMUSG-UHFFFAOYSA-K [B+3].[F-].[F-].[F-] Chemical compound [B+3].[F-].[F-].[F-] UGJVZXBXVRMUSG-UHFFFAOYSA-K 0.000 description 1
- BPIKJNDDLGCDJK-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)NN=C(C(=O)OC)CC1=CC=CC=C1 Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)NN=C(C(=O)OC)CC1=CC=CC=C1 BPIKJNDDLGCDJK-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- MXOAEAUPQDYUQM-UHFFFAOYSA-N chlorphenesin Chemical group OCC(O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- QJUXBIVLOGRZSQ-OQMMLGNJSA-N eliq Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1.C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 QJUXBIVLOGRZSQ-OQMMLGNJSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- KKVSEFNKUVENSF-UHFFFAOYSA-N ethyl 1-methyl-5-nitro-3-phenylindole-2-carboxylate Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)C(C(=O)OCC)=C1C1=CC=CC=C1 KKVSEFNKUVENSF-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- BJBDTTFQBKOQBG-UHFFFAOYSA-N ethyl 3-(2-bromophenyl)-5-nitro-1H-indole-2-carboxylate Chemical compound CCOC(C(NC(C1=C2)=CC=C2[N+]([O-])=O)=C1C(C=CC=C1)=C1Br)=O BJBDTTFQBKOQBG-UHFFFAOYSA-N 0.000 description 1
- IWHNFZHCVPXASB-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-5-nitro-1H-indole-2-carboxylate Chemical compound C(C)OC(=O)C=1NC2=CC=C(C=C2C1C1=CC=C(C=C1)Cl)[N+](=O)[O-] IWHNFZHCVPXASB-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 229960001269 glycine hydrochloride Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- UPAXKMALDDDKDR-UHFFFAOYSA-N methyl 1-methyl-5-nitro-3-phenylindole-2-carboxylate Chemical compound CN1C(=C(C2=CC(=CC=C12)[N+](=O)[O-])C1=CC=CC=C1)C(=O)OC UPAXKMALDDDKDR-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- HZQDHBGMMKYQDP-UHFFFAOYSA-N n-(2-benzoylphenyl)-2-bromoacetamide Chemical class BrCC(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 HZQDHBGMMKYQDP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229940073020 nitrol Drugs 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- OEAZJVWLSMMPPH-UHFFFAOYSA-N tert-butyl 2-oxo-3-phenylpropanoate Chemical compound CC(C)(C)OC(=O)C(=O)CC1=CC=CC=C1 OEAZJVWLSMMPPH-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE724727 | 1968-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE724727A true BE724727A (enrdf_load_html_response) | 1969-05-02 |
Family
ID=3853905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE724727D BE724727A (enrdf_load_html_response) | 1968-11-29 | 1968-11-29 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE724727A (enrdf_load_html_response) |
-
1968
- 1968-11-29 BE BE724727D patent/BE724727A/fr not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: SUMITOMO CHEMICAL CY LTD Effective date: 19841129 |