2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → Ethyl 2-methyl-4-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)nicotinate

HRID 890473노트

반응식

HRID 890473 반응식
[F:1][C:2]([F:19])([F:18])/[C:3](/O)=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[CH2:20]([O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26])[CH3:21]>C(#N)C>[CH2:20]([O:22][C:23](=[O:28])[C:24]1[C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:27][C:25]=1[CH3:26])[CH3:21]

참가 물질

4

반응물 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 178520887HCID 178520887, 화합물

생성물 1

HCID 86597779Ethyl 2-methyl-4-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)nicotinate수율 35%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To an acetonitrile (50 ml) solution of (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethyl-phenyl)-but-2-en-1-one (4.7 g, 17 mmol; D. Barrett, P. D. Bentley, T. R. Perrior, Synthetic Commun. 1996, 26, 3401–3406) was added ethyl-3-aminocrotonate (4.27 g, 33 mmol) under an argon atmosphere. The mixture was heated at reflux for 12 h. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, n-heptane/ethyl acetate) to yield 2.2 g (5.8 mmol, 35%) of the title compound as yellow crystals.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography (silica gel, n-heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-7b2a2b51e622453b9cc629fa565e5ec8
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995263B2

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