Hydrochloric Acid → 4-Phenyl-3-(1-Phenylvinyl)-8-(Trifluoromethyl)Quinoline

HRID 2104596노트

반응식

HRID 2104596 반응식
[C:1]1([C:7]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:29])([F:28])[F:27])(O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O>CCO>[C:20]1([C:19]2[C:18]3[C:13](=[C:14]([C:26]([F:29])([F:27])[F:28])[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][C:10]=2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH2:8])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 113498961-Phenyl-1-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]ethanol

생성물 1

HCID 669135304-Phenyl-3-(1-Phenylvinyl)-8-(Trifluoromethyl)Quinoline수율 85%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1-phenyl-1-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]ethanol (0.675 g, 1.72 mmol) in EtOH (13 mL) is refluxed with conc HCl (2.6 mL) for 2 h. The cooled reaction is poured into water and extracted with methylene chloride. The extract is washed with saturated aq sodium bicarbonate, dried (MgSO4) and concentrated. The residue is chromatographed eluting with 5:95 ethyl acetate:hexane to afford the title compound as a yellow solid (0.546 g, 85%). MS (ESI) m/z 376; HRMS: calcd for C24H16F3N+H, 376.13131; found (ESI, [M+H]+), 376.1306.

후처리

  1. customThe cooled reaction
  2. extractionextracted with methylene chloride
  3. washThe extract is washed with saturated aq sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed
  7. washeluting with 5:95 ethyl acetate

출처 및 근거

ORD 기록
ord-fdb8d05f91564052b6024c70a47bd1a3
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576215B2

반응 노트

불러오는 중…