SU538663A3 - Способ получени алкил-6,7-диалкокси-2-метил-4-оксотетрагидрохинолин1-карбоксилатов - Google Patents

Способ получени алкил-6,7-диалкокси-2-метил-4-оксотетрагидрохинолин1-карбоксилатов

Info

Publication number: SU538663A3
Authority: SU; USSR - Soviet Union
Prior art keywords: methyl; oxotetrahydroquinoline; dialkoxy; carboxylates; ethyl
Prior art date: 1973-12-26

Application number

SU2098256A

Other languages

English (en)

Russian (ru)

Inventor

Арман Харберт Чарльз

Original Assignee

Пфайзер Инк (Фирма)

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.)

1973-12-26

Filing date

1974-12-25

Publication date

1976-12-05

1974-12-25 Application filed by Пфайзер Инк (Фирма) filed Critical Пфайзер Инк (Фирма)

1976-12-05 Application granted granted Critical

1976-12-05 Publication of SU538663A3 publication Critical patent/SU538663A3/ru

Links

238000004519 manufacturing process Methods 0.000 title 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
239000000203 mixture Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000002253 acid Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
-1 (3,4-dimethoxy) -aniline-butane Chemical compound 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000002904 solvent Substances 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 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Quinoline Compounds (AREA)

SU2098256A 1973-12-26 1974-12-25 Способ получени алкил-6,7-диалкокси-2-метил-4-оксотетрагидрохинолин1-карбоксилатов SU538663A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US42844173A	1973-12-26	1973-12-26

Publications (1)

Publication Number	Publication Date
SU538663A3 true SU538663A3 (ru)	1976-12-05

Family

ID=23698907

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU2098256A SU538663A3 (ru)	1973-12-26	1974-12-25	Способ получени алкил-6,7-диалкокси-2-метил-4-оксотетрагидрохинолин1-карбоксилатов

Country Status (21)

Country	Link
JP (1)	JPS582937B2 (fr)
AR (1)	AR205807A1 (fr)
BE (1)	BE823811A (fr)
CA (1)	CA1035360A (fr)
DD (1)	DD117454A5 (fr)
DE (1)	DE2461050C2 (fr)
DK (1)	DK138889B (fr)
ES (1)	ES433305A1 (fr)
FI (1)	FI368374A7 (fr)
FR (1)	FR2255906B1 (fr)
GB (1)	GB1454039A (fr)
HU (1)	HU169380B (fr)
IE (1)	IE40329B1 (fr)
IL (1)	IL46232A0 (fr)
LU (1)	LU71558A1 (fr)
NL (1)	NL7416666A (fr)
NO (1)	NO744670L (fr)
RO (1)	RO64270A (fr)
SE (1)	SE421417B (fr)
SU (1)	SU538663A3 (fr)
ZA (1)	ZA748171B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3978064A (en) *	1975-11-04	1976-08-31	Pfizer Inc.	3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto

1974
- 1974-01-01 AR AR257070A patent/AR205807A1/es active
- 1974-09-13 GB GB4012674A patent/GB1454039A/en not_active Expired
- 1974-12-10 SE SE7415497A patent/SE421417B/xx unknown
- 1974-12-12 IL IL46232A patent/IL46232A0/xx unknown
- 1974-12-12 IE IE2561/74A patent/IE40329B1/xx unknown
- 1974-12-16 DK DK653874AA patent/DK138889B/da unknown
- 1974-12-19 FI FI3683/74A patent/FI368374A7/fi unknown
- 1974-12-20 DE DE2461050A patent/DE2461050C2/de not_active Expired
- 1974-12-20 HU HUPI440A patent/HU169380B/hu unknown
- 1974-12-20 NL NL7416666A patent/NL7416666A/xx not_active Application Discontinuation
- 1974-12-23 NO NO744670A patent/NO744670L/no unknown
- 1974-12-23 ZA ZA00748171A patent/ZA748171B/xx unknown
- 1974-12-24 DD DD183378A patent/DD117454A5/xx unknown
- 1974-12-24 CA CA216,781A patent/CA1035360A/fr not_active Expired
- 1974-12-24 LU LU71558A patent/LU71558A1/xx unknown
- 1974-12-24 BE BE1006357A patent/BE823811A/fr unknown
- 1974-12-24 ES ES433305A patent/ES433305A1/es not_active Expired
- 1974-12-25 SU SU2098256A patent/SU538663A3/ru active
- 1974-12-26 FR FR7442911A patent/FR2255906B1/fr not_active Expired
- 1974-12-26 JP JP752045A patent/JPS582937B2/ja not_active Expired
- 1974-12-26 RO RO7480945A patent/RO64270A/fr unknown

Also Published As

Publication number	Publication date
DE2461050A1 (de)	1975-07-17
JPS582937B2 (ja)	1983-01-19
GB1454039A (en)	1976-10-27
IE40329L (en)	1975-06-26
ZA748171B (en)	1976-01-28
DD117454A5 (fr)	1976-01-12
DK138889B (da)	1978-11-13
LU71558A1 (fr)	1975-08-20
BE823811A (fr)	1975-06-24
FI368374A7 (fr)	1975-06-27
JPS50105672A (fr)	1975-08-20
AU7658174A (en)	1976-06-24
FR2255906A1 (fr)	1975-07-25
HU169380B (fr)	1976-11-28
IL46232A0 (en)	1975-03-13
FR2255906B1 (fr)	1978-06-30
IE40329B1 (en)	1979-05-09
DK138889C (fr)	1979-04-30
NL7416666A (nl)	1975-06-30
AR205807A1 (es)	1976-06-07
SE421417B (sv)	1981-12-21
RO64270A (fr)	1979-05-15
CA1035360A (fr)	1978-07-25
SE7415497L (fr)	1975-06-27
DE2461050C2 (de)	1983-12-29
NO744670L (fr)	1975-07-21
DK653874A (fr)	1975-08-25
ES433305A1 (es)	1977-03-01

Publication	Publication Date	Title
SU764610A3 (ru)	1980-09-15	Способ получени производных 2-ароил-3-фенилбензотиофенов или их солей
NZ199967A (en)	1985-08-30	Benzofuran derivatives and pharmaceutical compositions
US3953490A (en)	1976-04-27	Preparation of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile
SU538663A3 (ru)	1976-12-05	Способ получени алкил-6,7-диалкокси-2-метил-4-оксотетрагидрохинолин1-карбоксилатов
JPH0354945B2 (fr)	1991-08-21
NO147809B (no)	1983-03-07	Kraftturbin.
SU1055333A3 (ru)	1983-11-15	Способ получени алкалоидов типа лейрозина или их кислых аддитивных солей
NO166712B (no)	1991-05-21	Fremgangsmaate ved fremstilling av pyrrolidonderivater.
DD143768A5 (de)	1980-09-10	Verfahren zur herstellung von pyrrolidon-verbindungen
KR102283391B1 (ko)	2021-07-30	데커신 유도체의 신규 합성방법
Pozdnev	1990	Improved method for synthesis of 7-amino-4-methylcoumarin
SU692561A3 (ru)	1979-10-15	Способ получени производных 2нитро-8-фенилбензофурана
KR890003840B1 (ko)	1989-10-05	8-할로-5, 6-디알콜시퀴나졸린-2, 4-디온의 제조방법
US4988822A (en)	1991-01-29	Intermediates for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo(1,2-A)pyrrole-1,1-dicarboxylates
SU502607A3 (ru)	1976-02-05	Способ получени лактамов
US3809700A (en)	1974-05-07	Certain 5,6-dioxopyrrolo(2,1-b)thiazoles
SU576043A3 (ru)	1977-10-05	Способ получени -оксиметил-2-нитроимидазола
US4079065A (en)	1978-03-14	Process for the production of 2H-cyclopenta (b) furan-2-one compounds
US3412109A (en)	1968-11-19	Process for 2-alkoxy-2, 3-dihydro 5-benzofuranols
CA1327042C (fr)	1994-02-15	Procede pour la preparation de thiazolabenzimidazoles et intermediaires utilises a cette fin
SU920056A1 (ru)	1982-04-15	Способ получени R,S-2,3,5,6-тетрагидро-6-фенилимидазо /2.1-в/-тиазола
KR100209293B1 (ko)	1999-07-15	제초성 피리미딜옥시벤조산 옥심에스테르 유도체의 신규한 제조방법
US3786068A (en)	1974-01-15	Intermediate in the total synthesis of elenolic acid
US4029664A (en)	1977-06-14	Process for interconversion of heteroyohimbane alkaloids
GB2281297A (en)	1995-03-01	Quinazoline compounds