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

HRID 2104596ノート

反応式

HRID 2104596 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fdb8d05f91564052b6024c70a47bd1a3
出典データセット
uspto-grants-2009_08
特許番号
US07576215B2

反応ノート

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