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

HRID 1097783Notes

Reaction equation

HRID 1097783 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-524e56e28f8d4ae6bd17bd4c79a6b74d
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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