KR960041164A - 4-트리플루오로메틸니코틴산의 제조 방법 - Google Patents

4-트리플루오로메틸니코틴산의 제조 방법 Download PDF

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KR960041164A
KR960041164A KR1019960017889A KR19960017889A KR960041164A KR 960041164 A KR960041164 A KR 960041164A KR 1019960017889 A KR1019960017889 A KR 1019960017889A KR 19960017889 A KR19960017889 A KR 19960017889A KR 960041164 A KR960041164 A KR 960041164A
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도루 고야나기
데쯔오 요네다
후미오 가나모리
시게히사 간바야시
도요시 다니무라
노리유끼 호리우찌
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아끼자와 다까시
이시하라 산교 가부시끼가이샤
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
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    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
    • C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
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    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups

Abstract

(ⅰ) 염기의 존재하에 하기 식(Ⅰ)의 할라이드를 하기 식(Ⅱ)의 화합물과 반응시켜 하기 식(Ⅲ)의 4-알콕시-1,1,1-트리플루오로-3-부텐-2-온을 얻고, 이 화합물을 암모니아와 반응시켜 하기 식(Ⅳ)의 4-아미노-1,1,1-트리플루오로-3-부텐-2-온을 얻는 제1단계,
CF3COHal (Ⅰ)
(식 중, Hal은 할로겐 원자임)
CH2=CHOR1(Ⅱ)
(식 중, R1은 알킬기임)
CF3CO-CH=CH-OR1(Ⅲ)
(R1은 상기 정의한 바와 같음)
및 (ⅱ) 제1단계에서 얻은 4-아미노-1,1,1-트리플루오로-3-부텐-2온과 하기 식(Ⅴ)의 화합물을 축합반응시켜 반응산물로서 하기 식(Ⅳ)의 화합물(그의 염 포함) 및(또는) 하기 식(Ⅶ)의 화합물(그의 염 포함)을 얻고, 이어서 반응산물을 폐환 및 가수분해 반응시키는 제2단계로 이루어지는 하기 식(Ⅷ)의 4-트리플루오로메틸니코틴산 또는 그의 염의 제조방법.
ACO2R2(Ⅴ)
(식 중, R2는 에스테르-형성 잔기이며, A는 (R3O)CH=CH- 또는 (R3O)2CHCH2-이며, 여기서 R3는 알킬기임)
(식 중, R2는 상기 정의한 바와 같음)
(식 중, R2및 R3는 상기 정의한 바와 같음)

Description

4-트리플루오로메틸니코틴산의 제조 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (18)

  1. (ⅰ) 염기의 존재하에 하기 식(Ⅰ)의 할라이드를 하기 식(Ⅱ)의 화합물과 반응시켜 하기 식(Ⅲ)의 4-알콕시-1,1,1-트리플루오로-3-부텐-2-온을 얻고, 이 화합물을 암모니아와 반응시켜 하기 식(Ⅳ)의 4-아미노-1,1,1-트리플루오로-3-부텐-2-온을 얻는 제1단계,
    CF3COHal (Ⅰ)
    (식 중, Hal은 할로겐 원자임)
    CH2=CHOR1(Ⅱ)
    (식 중, R1은 알킬기임)
    CF3CO-CH=CH-OR1(Ⅲ)
    (R1은 상기 정의한 바와 같음)
    및 (ⅱ) 제1단계에서 얻은 4-아미노-1,1,1-트리플루오로-3-부텐-2-온과 하기 식(Ⅴ)의 화합물을 축합반응시켜 반응산물로서 하기 식(Ⅵ)의 화합물(그의 염 포함) 및(또는) 하기 식(Ⅶ)의 화합물(그의 염 포함)을 얻고, 이어서 반응산물을 폐환 및 가수분해 반응시키는 제2단계로 이루어지는 하기 식(Ⅷ)의 4-트리플루오로메틸니코틴산 또는 그의 염을 제조 방법.
    ACO2R2(Ⅴ)
    (식 중, R2는 에스테르-형성 잔기이며, A는 (R3O)CH=CH- 또는 (R3O)2CHCH2-이며, 여기서 R3는 알킬기임)
    (식 중, R2는 상기 정의한 바와 같음)
    (식 중, R2및 R3는 상기 정의한 바와 같음)
  2. 염기의 존재하에 하기 식(Ⅰ)의 할라이드와 하기 식(Ⅱ)의 화합물을 반응시키는 것으로 이루어지는 하기 식(Ⅲ)의 4-알콕시-1,1,1-트리플루오로-3-부텐-2-온의 제조 방법.
    CF3COHal (Ⅰ)
    (식 중, Hal은 할로겐 원자임)
    CH2=CHOR1(Ⅱ)
    (식 중, R1은 알킬기임)
    CF3CO-CH=CH-OR1(Ⅲ)
    (R1은 상기 정의한 바와 같음)
  3. 염기의 존재하에 하기 식(Ⅰ)의 할라이드와 하기 식(Ⅱ)의 화합물을 반응시켜 하기 식(Ⅲ)의 4-알콕시-1,1,1-트리플루오로-3-부텐-2-온을 얻고, 이 화합물을 암모니아와 반응시키는 것으로 이루어지는 4-아미노-1,1,1-트리플루오로-3-부텐-2-온의 제조 방법.
    CF3COHal (Ⅰ)
    (식 중, Hal은 할로겐 원자임)
    CH2=CHOR1(Ⅱ)
    (식 중, R1은 알킬기임)
    CF3CO-CH=CH-OR1(Ⅲ)
    (R1은 상기 정의한 바와 같음)
  4. 하기 식(Ⅳ)의 4-아미노-1,1,1-트리플루오로-3-부텐-2-온과 하기 식(Ⅴ)의 화합물을 축합 반응시켜 반응산물로서 하기 식(Ⅵ)의 화합물(그의 염 포함) 및(또는) 하기 식(Ⅶ)의 화합물(그의 염 포함)을 얻고, 이어서 반응산물을 폐환 및 가수분해 반응시키는 것으로 이루어지는 하기 식(Ⅷ)의 4-트리플루오로메틸니코틴산 또는 그의 염의 제조 방법.
    (식 중, R2는 에스테르-형성 잔기이며, A는 (R3O)CH=CH- 또는 (R3O)2CHCH2-이며, 여기서 R3는 알킬기임)
    (식 중, R2는 상기 정의한 바와 같음)
    (식 중, R2및 R3는 상기 정의한 바와 같음)
  5. 제1항에 있어서, 식(Ⅰ)의 할라이드가 트리플루오로아세틸 클로라이드인 방법.
  6. 제1항에 있어서, 식(Ⅲ)의 화합물을 단리하지 않고 암모니아와 반응시키는 방법.
  7. 제1항에 있어서, 반응에 사용하는 암모니아가 암모니아 가스인 방법.
  8. 제1항에 있어서, 식(Ⅰ)의 할라이드와 식(Ⅱ)의 화합물의 반응에 용매를 사용하는 방법.
  9. 제1항에 있어서, 식(Ⅳ)의 화합물과 하기 식(Ⅴ-1)의 화합물을 축합 반응시키는 방법.
    (R3O)2CHCH2CO2R2(Ⅴ-1)
    (식 중, R2는 에스테르-형성 잔기이며, R3는 알킬기임)
  10. 제1항에 있어서, 염기 또는 산의 존재하에 식(Ⅳ)의 화합물과 하기 식(Ⅴ-2)의 화합물을 축합 반응시키는 방법.
    (R3O)CH=CHCO2R3(Ⅴ-2)
    (식 중, R2는 에스테르-형성 잔기이며, R3는 알킬기임)
  11. 제9항에 있어서, 염기 및(또는) 용매의 존재하에 축합 반응을 수행하는 방법.
  12. 제10항에 있어서, 용매의 존재하에 축합 반응을 수행하는 방법.
  13. 제1항에 있어서, 염기 및(또는) 용매의 존재하에 폐환 및 가수반해 반응을 수행하는 방법.
  14. 제1항에 있어서, 축합 반응에서 식(Ⅴ)의 화합물을 식(Ⅵ)의 화합물 몰 당 1.0 내지 1.2몰의 양으로 사용하는 방법.
  15. 식(Ⅵ)의 화합물(그의 염 포함) 및(또는) 식 (Ⅶ)의 화합물(그의 염 포함)을 폐환 및 가수분해 반응시키는 것으로 이루어지는 식(Ⅷ)의 4-트리플루오로메틸니코틴산 또는 그의 염의 제조 방법.
    (식 중, R2는 에스테르-형성 잔기임)
    (식 중, R2는 상기 정의한 바와 같으며, R3는 알킬기임)
  16. 식(Ⅵ)의 화합물 또는 그의 염.
    (식 중, R2는 에스테르-형성 잔기임)
  17. 식(Ⅵ')의 화합물 또는 그의 염.
    (식 중, R2는 에스테르-형성 잔기임)
  18. 식(Ⅶ)의 화합물 또는 그의 염.
    (식 중, R2는 에스테르-형성 잔기이며, R3는 알킬기임)
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960017889A 1995-05-26 1996-05-25 4-트리플루오로메틸니코틴산의제조방법 KR100381484B1 (ko)

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CA2176788C (en) 2007-01-09
US5708175A (en) 1998-01-13
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