2-Quinolinecarboxaldehyde → 2-Quinolinemethanol

HRID 351601

反応式

HRID 351601 の反応式
[BH4-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH:13]=[O:14]>C(O)C>[OH:14][CH2:13][CH:4]1[CH2:5][CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:3]1.[OH:14][CH2:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]=1

参加物

5

反応物 2

HCID 796192-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

生成物 2

HCID 731962-QuinolinemethanolHCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Sodium borohydride (21.7 g, 0.57 mol) was added in portions to a solution of quinoline-2-carboxaldehyde (30 g, 0.191 mol) in ethanol (300 mL) at 0° C. The reaction mixture was warmed to room temperature, stirred at room temperature for 2 hrs, and quenched by water. Volatiles were removed under reduced pressure and the residue dissolved in ethyl acetate, washed with water and saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide the desired compound and 2-(hydroxymethyl)quinoline. A solution of the recovered 2-(hydroxymethyl)quinoline in ethanol (250 mL) and tetrahydrofuran (250 mL) was hydrogenated at 60 psi in the presence of 5% platinum on carbon at 40° C. for 48 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to provide the title compound.

後処理

  1. customquenched by water
  2. customVolatiles were removed under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f6f7b93775e143ccb92bc7a447b47d8b
出典データセット
uspto-grants-2004_06
特許番号
US06743785B2

関連ノート

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