JPS634532B2 - - Google Patents

Info

Publication number: JPS634532B2
Authority: JP; Japan
Prior art keywords: reaction; substituted; formula; aminoisoquinoline; oxide
Prior art date: 1980-03-06
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

Application number

JP55027385A

Other languages

English (en)

Japanese (ja)

Other versions

JPS56123969A (en

Inventor

Chikara Kaneko

Masanori Somei

Yoshio Karasawa

Kawako Okuda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Daiichi Kagaku Yakuhin Co Ltd

Original Assignee

Daiichi Kagaku Yakuhin Co Ltd

Priority date (The priority date 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 date listed.)

1980-03-06

Filing date

1980-03-06

Publication date

1988-01-29

1980-03-06 Application filed by Daiichi Kagaku Yakuhin Co Ltd filed Critical Daiichi Kagaku Yakuhin Co Ltd

1980-03-06 Priority to JP2738580A priority Critical patent/JPS56123969A/ja

1981-09-29 Publication of JPS56123969A publication Critical patent/JPS56123969A/ja

1988-01-29 Publication of JPS634532B2 publication Critical patent/JPS634532B2/ja

Status Granted legal-status Critical Current

Links

238000006243 chemical reaction Methods 0.000 claims description 20
-1 N-substituted-4-hydroxyindoles Chemical class 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
239000002994 raw material Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 7
NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
DTVYNUOOZIKEEX-UHFFFAOYSA-N 5-aminoisoquinoline Chemical compound N1=CC=C2C(N)=CC=CC2=C1 DTVYNUOOZIKEEX-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
SESKAGIATRJFHN-UHFFFAOYSA-N 2-oxidoisoquinolin-2-ium-5-amine Chemical class [O-][N+]1=CC=C2C(N)=CC=CC2=C1 SESKAGIATRJFHN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000010446 mirabilite Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
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 4
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012450 pharmaceutical intermediate Substances 0.000 description 3
239000005297 pyrex Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
150000001204 N-oxides Chemical class 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HDCDVKFQYKJZFG-UHFFFAOYSA-N benzyl 4-hydroxyindole-1-carboxylate Chemical compound C1=CC=2C(O)=CC=CC=2N1C(=O)OCC1=CC=CC=C1 HDCDVKFQYKJZFG-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
150000002475 indoles Chemical class 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 description 1
RYWYLFSBHZEAJD-UHFFFAOYSA-N 2-hydroxy-6-nitrobenzaldehyde Chemical compound OC1=CC=CC([N+]([O-])=O)=C1C=O RYWYLFSBHZEAJD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229940054051 antipsychotic indole derivative Drugs 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
238000009835 boiling Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
AWGPUYVDLAIILL-UHFFFAOYSA-N ethyl n-isoquinolin-5-ylcarbamate Chemical compound N1=CC=C2C(NC(=O)OCC)=CC=CC2=C1 AWGPUYVDLAIILL-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000006552 photochemical reaction Methods 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Landscapes

Indole Compounds (AREA)

JP2738580A 1980-03-06 1980-03-06 4-hydroxyindole derivative and its preparation Granted JPS56123969A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP2738580A JPS56123969A (en)	1980-03-06	1980-03-06	4-hydroxyindole derivative and its preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2738580A JPS56123969A (en)	1980-03-06	1980-03-06	4-hydroxyindole derivative and its preparation

Publications (2)

Publication Number	Publication Date
JPS56123969A JPS56123969A (en)	1981-09-29
JPS634532B2 true JPS634532B2 (2)	1988-01-29

Family

ID=12219577

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2738580A Granted JPS56123969A (en)	1980-03-06	1980-03-06	4-hydroxyindole derivative and its preparation

Country Status (1)

Country	Link
JP (1)	JPS56123969A (2)

1980
- 1980-03-06 JP JP2738580A patent/JPS56123969A/ja active Granted

Also Published As

Publication number	Publication date
JPS56123969A (en)	1981-09-29

Publication	Publication Date	Title
JPS5995231A (ja)	1984-06-01	光学活性化合物の製造方法
JPS634532B2 (2)	1988-01-29
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Apple et al.	2002	2-Aminobenzaldehydes from quinolinium salts and alkaline hydrogen peroxide
HU181503B (en)	1983-10-28	Process for producing 3,3-ethylenedioxy-4,5-seco-19-nor-androst-9-ene-5,17-dione
CN115872923A (zh)	2023-03-31	一种化合物及其制备方法
US3429897A (en)	1969-02-25	3,6-dihydro-1,2-dioxin and its method of production
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