N-benzoyl-1,2-dihydroquinolin-4(3H)-one → N-benzoyl-1,2,3,4-tetrahydroquinolin-4-ol

HRID 1097783ノート

反応式

HRID 1097783 の反応式
[BH4-].[Na+].[C:3]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[CH2:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[OH:21][CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]([C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:10])[CH2:12][CH2:13]1

参加物

4

反応物 2

HCID 283524N-benzoyl-1,2-dihydroquinolin-4(3H)-oneHCID 4311764Sodium borohydride

生成物 1

HCID 59277722N-benzoyl-1,2,3,4-tetrahydroquinolin-4-ol収率 84.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

NaBH4 (85 mg, 2.25 mmol) is added to a solution of 1-benzoyl-2,3-dihydro-1H-quinolin-4-one (from step C) in methanol (5 mL) at 0° C. The resulting mixture is stirred at room temperature. After 1 h, the reaction is quenched by 1 N HCl. The solvent is removed under vacuum. The residue is taken up in CH2Cl2 and washed by brine, and dried over anhydrous sodium sulfate. After concentration, the residue is purified by flash chromatography to give the title compound (380 mg, 84.8% yield for the two steps).

後処理

  1. customthe reaction is quenched by 1 N HCl
  2. customThe solvent is removed under vacuum
  3. washwashed by brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue is purified by flash chromatography

出典と根拠

ORDレコード
ord-524e56e28f8d4ae6bd17bd4c79a6b74d
出典データセット
uspto-grants-2012_03
特許番号
US08143278B2

反応ノート

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