JPH0149150B2 - - Google Patents
Info
- Publication number
- JPH0149150B2 JPH0149150B2 JP7262782A JP7262782A JPH0149150B2 JP H0149150 B2 JPH0149150 B2 JP H0149150B2 JP 7262782 A JP7262782 A JP 7262782A JP 7262782 A JP7262782 A JP 7262782A JP H0149150 B2 JPH0149150 B2 JP H0149150B2
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- acetonitrile
- acetic acid
- solvent
- water
- 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.)
- Expired
Links
- -1 4-substituted indole acetic acid Chemical class 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000010446 mirabilite Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- ZQFPMQFVJBELCS-UHFFFAOYSA-N 2-(4-iodo-1h-indol-3-yl)acetic acid Chemical compound C1=CC(I)=C2C(CC(=O)O)=CNC2=C1 ZQFPMQFVJBELCS-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- ZLBIYQIVGWLJHO-UHFFFAOYSA-N methyl 3-(cyanomethyl)-4-nitroindole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)C=C(CC#N)C2=C1[N+]([O-])=O ZLBIYQIVGWLJHO-UHFFFAOYSA-N 0.000 description 4
- POJGICIDBWHZSQ-UHFFFAOYSA-N methyl 4-amino-3-(cyanomethyl)indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)C=C(CC#N)C2=C1N POJGICIDBWHZSQ-UHFFFAOYSA-N 0.000 description 4
- WJLZJGWWMSKGKY-UHFFFAOYSA-N 1-(4-bromo-1h-indol-3-yl)-n,n-dimethylmethanamine Chemical compound C1=CC(Br)=C2C(CN(C)C)=CNC2=C1 WJLZJGWWMSKGKY-UHFFFAOYSA-N 0.000 description 3
- AQIDQZFQDRENOY-UHFFFAOYSA-N 2-(4-bromo-1h-indol-3-yl)acetic acid Chemical compound C1=CC(Br)=C2C(CC(=O)O)=CNC2=C1 AQIDQZFQDRENOY-UHFFFAOYSA-N 0.000 description 3
- ILCMRTYGNSGRBS-UHFFFAOYSA-N 2-(4-nitro-1h-indol-3-yl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(CC#N)=CN2 ILCMRTYGNSGRBS-UHFFFAOYSA-N 0.000 description 3
- LAVZKLJDKGRZJG-UHFFFAOYSA-N 4-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC2=C1C=CN2 LAVZKLJDKGRZJG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- RCEOZHBLULRIST-UHFFFAOYSA-N methyl 3-(cyanomethyl)-4-iodoindole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)C=C(CC#N)C2=C1I RCEOZHBLULRIST-UHFFFAOYSA-N 0.000 description 3
- NTWUAOHAQNZERF-UHFFFAOYSA-N n,n-dimethyl-1-(4-nitro-1h-indol-3-yl)methanamine Chemical compound C1=CC([N+]([O-])=O)=C2C(CN(C)C)=CNC2=C1 NTWUAOHAQNZERF-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CGFUOBNYUICDPH-UHFFFAOYSA-N 2-(4-bromo-1h-indol-3-yl)acetonitrile Chemical compound BrC1=CC=CC2=C1C(CC#N)=CN2 CGFUOBNYUICDPH-UHFFFAOYSA-N 0.000 description 2
- GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-UHFFFAOYSA-N 0.000 description 2
- WNCFBCKZRJDRKZ-UHFFFAOYSA-N 4-chloroindole-3-acetic acid Chemical compound C1=CC(Cl)=C2C(CC(=O)O)=CNC2=C1 WNCFBCKZRJDRKZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- 238000000297 Sandmeyer reaction Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
- 238000006063 methoxycarbonylation reaction Methods 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- FPBHXYPVNWHLHT-UHFFFAOYSA-N 2-(4-iodo-1h-indol-3-yl)acetonitrile Chemical compound IC1=CC=CC2=C1C(CC#N)=CN2 FPBHXYPVNWHLHT-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
- 239000003563 4-chloroindole-3-acetic acid Substances 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003617 indole-3-acetic acid Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RUGAULALUBLSEG-UHFFFAOYSA-N methyl 4-aminoindole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)C=CC2=C1N RUGAULALUBLSEG-UHFFFAOYSA-N 0.000 description 1
- QLNAOKSQDONCTG-UHFFFAOYSA-N methyl 4-bromo-3-(cyanomethyl)indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)C=C(CC#N)C2=C1Br QLNAOKSQDONCTG-UHFFFAOYSA-N 0.000 description 1
- YNYACKHOGSXQKR-UHFFFAOYSA-N methyl 4-bromoindole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)C=CC2=C1Br YNYACKHOGSXQKR-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7262782A JPS58189161A (ja) | 1982-04-30 | 1982-04-30 | ４位置換インド−ル誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7262782A JPS58189161A (ja) | 1982-04-30 | 1982-04-30 | ４位置換インド−ル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58189161A JPS58189161A (ja) | 1983-11-04 |
| JPH0149150B2 true JPH0149150B2 (sh) | 1989-10-23 |
Family
ID=13494807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7262782A Granted JPS58189161A (ja) | 1982-04-30 | 1982-04-30 | ４位置換インド−ル誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58189161A (sh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5674731A (en) * | 1995-04-27 | 1997-10-07 | Life Technologies, Inc. | Regeneration of both plant tissues and transgenic plant tissues using a new plant hormone, 5-bromoindole-3-acetic acid |
| JP3943661B2 (ja) * | 1996-07-11 | 2007-07-11 | 株式会社資生堂 | インドール誘導体及びこれを有効成分とする発根誘導剤 |
-
1982
- 1982-04-30 JP JP7262782A patent/JPS58189161A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58189161A (ja) | 1983-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5128482A (en) | Process for the production of 3-1(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl) indole | |
| JP2825517B2 (ja) | 除草性ｏ―カルボキシアリ―ルイミダゾリノン類の製法 | |
| JPH0149150B2 (sh) | ||
| JPS63104957A (ja) | オクタヒドロインドール誘導体の製造方法 | |
| JPH0455427B2 (sh) | ||
| JPH0213669B2 (sh) | ||
| EP0713865B1 (fr) | Dérivés d'acide 2-aminobenzènesulfonique et de chlorure de 2-aminobenzènesulfonyle, leur préparation et leur utilisation comme intermédiaires de synthèse | |
| KR930010500B1 (ko) | 코타르닌의 제조방법 | |
| JP2958834B2 (ja) | アゼチジン−２−オン誘導体 | |
| JP2769058B2 (ja) | シクロプロパン誘導体の製法 | |
| JP2767295B2 (ja) | インドール―３―カルボニトリル化合物の製造方法 | |
| US20020198400A1 (en) | Synthesis of 3-amino-3-aryl propanoates | |
| JP3006237B2 (ja) | アミノピラゾール誘導体の製法 | |
| JPH06293700A (ja) | ６−クロロサリチル酸の製造法 | |
| JP2716243B2 (ja) | Ｎ―ベンジル―３―ヒドロキシスクシンアミド酸およびその製造法 | |
| JP2958835B2 (ja) | ４−（１−カルボキシアルキル）アゼチジン−２−オン誘導体の製造法 | |
| US3751462A (en) | Process for preparation of substituted fluoromethanesulfonanilides | |
| JPS62201866A (ja) | インド−ル酢酸誘導体の製造方法 | |
| JP2003137835A (ja) | （ｒ）−３−ヒドロキシ−３−（２−フェニルエチル）ヘキサン酸の製造方法 | |
| JPH0768194B2 (ja) | ５−（１−ブチン−３−イル）オキシ−４−クロロ−２−フルオロアセトアニリドおよびその製造法 | |
| JPH03127780A (ja) | アニリノピリミジン誘導体 | |
| FR2698355A1 (fr) | Nouveaux dérivés de 1-phénylbicyclo[2.2.2] octane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. | |
| JPH0655714B2 (ja) | ジフエニルチオエ−テル誘導体の製造法 | |
| JPH01100157A (ja) | インドール−３−カルボニトリル類の製造法 | |
| JPH0588223B2 (sh) |