KR960004323A - Method for preparing 4-ethoxycarbonyl-6,7-dihydro-5H-1-pyridine - Google Patents

Method for preparing 4-ethoxycarbonyl-6,7-dihydro-5H-1-pyridine Download PDF

Info

Publication number
KR960004323A
KR960004323A KR1019940016020A KR19940016020A KR960004323A KR 960004323 A KR960004323 A KR 960004323A KR 1019940016020 A KR1019940016020 A KR 1019940016020A KR 19940016020 A KR19940016020 A KR 19940016020A KR 960004323 A KR960004323 A KR 960004323A
Authority
KR
South Korea
Prior art keywords
compound
formula
ethoxycarbonyl
reacted
represented
Prior art date
Application number
KR1019940016020A
Other languages
Korean (ko)
Other versions
KR0131993B1 (en
Inventor
김중협
지대윤
김성훈
남길수
김하영
손현주
Original Assignee
김은영
한국과학기술 연구원
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.)
Filing date
Publication date
Application filed by 김은영, 한국과학기술 연구원 filed Critical 김은영
Priority to KR1019940016020A priority Critical patent/KR0131993B1/en
Publication of KR960004323A publication Critical patent/KR960004323A/en
Application granted granted Critical
Publication of KR0131993B1 publication Critical patent/KR0131993B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

본 발명은 일반식(Ⅰ)로 표시되는 4-에톡시카르보닐-6,7-디히드로-5H-1-피린딘의 제조방법에 관한 것으로, 나트륨을 알콜에 녹여 만든 나트륨알콕사이드와 반응시킨 에틸시아노아세테이트와 2-할로시클로펜타논을 반응시켜 (±)-2-(1-에톡시카르보닐-1-시아노메틸)시클로펜타논(Ⅲ)을 제조하고, 이 (Ⅲ)화합물을 에테르류의 용매 하에서 포타슘t-부톡사이드와 반응시키고, 이 중간체에 알릴할로겐을 반응시켜 (±)-2-시아노-2-(시클로펜타논-2-일)펜트-4-엔-카르복실산 에틸 에테르(Ⅳ)를 제조한 후 이 화합물(Ⅳ)를 오존과 반응시켜 (±)-2-시아노-2-(시클로펜타논-2-일)부탄-4-옥소-카르복실산 에틸 에스테르(Ⅴ)를 제조하고, 이 화합물(Ⅴ)를 히드록실아민과 반응시키고 연이어 포스포러스트리클로라이드로 반응시키는 것으로 이루어진다.The present invention relates to a method for producing 4-ethoxycarbonyl-6,7-dihydro-5H-1-pyridine represented by formula (I), wherein ethyl is reacted with sodium alkoxide made by dissolving sodium in alcohol. Cyanoacetate and 2-halocyclopentanone are reacted to prepare (±) -2- (1-ethoxycarbonyl-1-cyanomethyl) cyclopentanone (III), and the compound (III) is ether Reacted with potassium t-butoxide in a solvent of the same kind, and allylhalogen was reacted with this intermediate to give (±) -2-cyano-2- (cyclopentanone-2-yl) pent-4-ene-carboxylic acid. Ethyl ether (IV) was prepared, followed by reaction of this compound (IV) with ozone to give (±) -2-cyano-2- (cyclopentanon-2-yl) butane-4-oxo-carboxylic acid ethyl ester (V) is prepared and this compound (V) is reacted with hydroxylamine and subsequently with phosphorus chloride.

Description

4-에톡시카르보닐-6,7-디히드로-5H-1-피린딘의 제조방법Method for preparing 4-ethoxycarbonyl-6,7-dihydro-5H-1-pyridine

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (4)

나트륨을 녹인 알콜 용매하에서 일반식(Ⅱ)로 표시되는 2-할로시클로펜타논과 에틸 시아노 아세테이트를 반응시켜 일반식(Ⅲ)로 표시되는 (±)-2-(1-에톡시카르보닐-1-시아노메틸)시클로펜타논을 제조하은 제1단계; 상기 일반식(Ⅲ) 화합물과 알릴할라이드를 에테르 용매와 포타슘 t-부톡사이드 존재하에 반응시켜 일반식(Ⅳ)로 표시되는 (±)-2-시아노-2-(시클로펜타논-2-일)펜트-4-엔-카르복실산 에틸 에스테르를 제조하는 제2단계; 상기 일반식(Ⅳ)화합물을 오존과 반응시켜 일반식(Ⅴ)로 표시되는 (±)-2-시아노-2-(시클로펜타논-2-일)부탄-4-옥소-카르복실산 에틸 에스테르를 제조하는 3단계; 및 상기 일반식(Ⅴ)를 화합물에 히드록실아민염산염과 포스포러스트리클로 라이드를 반응시켜 제4단계로 이루어지는 일반식(Ⅰ)로 표시되는 4-에톡시카르보닐-6,7-디히드로-5H-1-피리딘의 제조방법.(±) -2- (1-ethoxycarbonyl-1 represented by formula (III) by reacting 2-halocyclopentanone represented by formula (II) with ethyl cyano acetate in an alcohol solvent in which sodium is dissolved A first step of preparing cyanomethyl) cyclopentanone; (±) -2-cyano-2- (cyclopentanone-2-yl represented by the general formula (IV) by reacting the general formula (III) compound and allyl halide in the presence of an ether solvent and potassium t-butoxide ) A second step of preparing a pent-4-ene-carboxylic acid ethyl ester; (±) -2-cyano-2- (cyclopentanon-2-yl) butane-4-oxo-carboxylic acid ethyl represented by the general formula (V) by reacting the compound of formula (IV) with ozone Three steps to prepare an ester; And 4-ethoxycarbonyl-6,7-dihydro-5H represented by the general formula (I) consisting of the fourth step by reacting the compound of formula (V) with a hydroxylamine hydrochloride and a phosphorus trichloride. Method for preparing -1-pyridine. 상기식에서 X는 할로겐이다.Wherein X is halogen. 제1항에 있어서, 상기 X가 클로로기인 제조방법.The method according to claim 1, wherein X is a chloro group. 제1항에 있어서, 상기 제1단계에서 알콜 용매가 에탄올인 제조방법.The method according to claim 1, wherein the alcohol solvent in the first step is ethanol. 제1항에 있어서, 상기 제2단계에서 에테르 용매가 테트라히드로퓨라인 제조방법.The method of claim 1, wherein the ether solvent in the second step is tetrahydropurine. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940016020A 1994-07-05 1994-07-05 Process for the preparation of substituted pyridine KR0131993B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019940016020A KR0131993B1 (en) 1994-07-05 1994-07-05 Process for the preparation of substituted pyridine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019940016020A KR0131993B1 (en) 1994-07-05 1994-07-05 Process for the preparation of substituted pyridine

Publications (2)

Publication Number Publication Date
KR960004323A true KR960004323A (en) 1996-02-23
KR0131993B1 KR0131993B1 (en) 1998-04-17

Family

ID=19387295

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940016020A KR0131993B1 (en) 1994-07-05 1994-07-05 Process for the preparation of substituted pyridine

Country Status (1)

Country Link
KR (1) KR0131993B1 (en)

Also Published As

Publication number Publication date
KR0131993B1 (en) 1998-04-17

Similar Documents

Publication Publication Date Title
KR860003227A (en) Method for preparing 9-amino-1,2,3,4, -tetrahydroacridin-1-ol
KR860001796A (en) Method for preparing α-aryl-4- (4,5-dihydro-3,5-dioxo-1,2,4-triazine-2 (3H) -yl) benzeneacetonitrile
KR850004492A (en) Method for preparing an enol ether derivative of oxycam
KR840002358A (en) Alpha 2-antagonistic pharmaceutical composition and method thereof
KR850002260A (en) Process for preparing substituted 4-alkyl-2 (1H) quinazolinone-1-alkanoic acid derivatives
KR850002459A (en) Dihydroxybenzamide derivatives and preparation method thereof
KR840001152A (en) Preparation of New Heterocyclic Compounds
KR960004323A (en) Method for preparing 4-ethoxycarbonyl-6,7-dihydro-5H-1-pyridine
KR860001097A (en) Method for preparing 4-amino-2-phenylquinoline
KR860001814A (en) Method for preparing imidazo [1.2-a] quinoline derivative
KR870003107A (en) Method for preparing chianthine derivative
CA2302381A1 (en) Process for producing 3,4-dihydroxy-3-cyclobutene-1,2-dione
KR850001903A (en) Method for preparing 2,6-disubstituted-1,4-dihydropyridine derivative and pharmaceutical composition comprising the same
KR910007861A (en) New ester compound and preparation method thereof
KR880000377A (en) Preparation method of trans hexahydro terephthalic acid ester derivative
KR850008163A (en) Method for preparing 2,4-diamino-6-halogeno-5-alkylthio-pyrimidine
KR960000883A (en) Novel Amine Compounds and Preparation Methods
KR970010774A (en) Method for preparing 7-amino-3-chloro-3-cepem-4-carboxylic acid
KR860002451A (en) Method for preparing an amide compound
KR960017605A (en) Method for preparing benzophenone derivative
KR850004581A (en) Method for preparing α, α-dimethylphenylacetanilide derivative
KR860000283A (en) Method for preparing pyridine derivative
KR830001899A (en) 4-amino-3-quinolinecarboxylic acid and ester-antisecretion, anti-ulcer compound
KR950032043A (en) Method for preparing allyl quinone derivatives and intermediates thereof
KR960017659A (en) New pyrrolidine derivatives and preparation methods thereof

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20030730

Year of fee payment: 7

LAPS Lapse due to unpaid annual fee