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

HRID 1097783노트

반응식

HRID 1097783 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-524e56e28f8d4ae6bd17bd4c79a6b74d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143278B2

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