JPS58189161A - ４位置換インド−ル誘導体 - Google Patents
４位置換インド−ル誘導体Info
- Publication number
- JPS58189161A JPS58189161A JP7262782A JP7262782A JPS58189161A JP S58189161 A JPS58189161 A JP S58189161A JP 7262782 A JP7262782 A JP 7262782A JP 7262782 A JP7262782 A JP 7262782A JP S58189161 A JPS58189161 A JP S58189161A
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- water
- acetonitrile
- acetic acid
- yield
- 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.)
- Granted
Links
- -1 4-substituted indole Chemical class 0.000 title claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 7
- 239000005648 plant growth regulator Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 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 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000013078 crystal Substances 0.000 description 15
- 239000010446 mirabilite Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 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 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KZEWCIGIMQFSBD-UHFFFAOYSA-N 2-(4-nitro-1H-indol-5-yl)acetonitrile Chemical compound [O-][N+](=O)C1=C(CC#N)C=CC2=C1C=CN2 KZEWCIGIMQFSBD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 239000000052 vinegar Substances 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 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
- LAVZKLJDKGRZJG-UHFFFAOYSA-N 4-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC2=C1C=CN2 LAVZKLJDKGRZJG-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 238000000297 Sandmeyer reaction Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000006063 methoxycarbonylation reaction Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LNDWMQWLWGXEET-UHFFFAOYSA-N 2-(1h-indol-5-yl)acetic acid Chemical class OC(=O)CC1=CC=C2NC=CC2=C1 LNDWMQWLWGXEET-UHFFFAOYSA-N 0.000 description 1
- SWFCZJVRWYZLPW-UHFFFAOYSA-N 2-(1h-indol-6-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C=CNC2=C1 SWFCZJVRWYZLPW-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
- JSMHPFAGQBYKJS-UHFFFAOYSA-N 3-methyl-4-nitro-1h-indole Chemical compound C1=CC([N+]([O-])=O)=C2C(C)=CNC2=C1 JSMHPFAGQBYKJS-UHFFFAOYSA-N 0.000 description 1
- GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-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
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 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 1
- 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 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 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 true JPS58189161A (ja) | 1983-11-04 |
| JPH0149150B2 JPH0149150B2 (enrdf_load_stackoverflow) | 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 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998002418A1 (fr) * | 1996-07-11 | 1998-01-22 | Shiseido Company, Ltd. | Derives d'indole et inducteurs d'enracinement contenant ces derniers sous forme de principe actif |
| EP0827532A4 (en) * | 1995-04-27 | 1999-05-12 | Life Technologies Inc | REGENERATION OF PLANT TISSUES AND TRANSGENIC PLANT TISSUES USING A NEW PLANT HORMONE, KNOWLEDGE OF 5-BROMOINDOLE-3-ACETIC ACID |
-
1982
- 1982-04-30 JP JP7262782A patent/JPS58189161A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0827532A4 (en) * | 1995-04-27 | 1999-05-12 | Life Technologies Inc | REGENERATION OF PLANT TISSUES AND TRANSGENIC PLANT TISSUES USING A NEW PLANT HORMONE, KNOWLEDGE OF 5-BROMOINDOLE-3-ACETIC ACID |
| WO1998002418A1 (fr) * | 1996-07-11 | 1998-01-22 | Shiseido Company, Ltd. | Derives d'indole et inducteurs d'enracinement contenant ces derniers sous forme de principe actif |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0149150B2 (enrdf_load_stackoverflow) | 1989-10-23 |
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