Sodium borohydride → HCID 59277701, compound

HRID 1097785Notes

Reaction equation

HRID 1097785 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])[C:13]([CH3:23])([CH3:22])[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][C:13]1([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59277720HCID 59277720, compound

Product 1

HCID 59277701HCID 59277701, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (306 mg, 8.09 mmol) is added to a solution of 1-benzoyl-3,3-dimethyl-2,3-dihydro-1H-quinolin-4-one (crude from step A) in MeOH (10 mL) at 0° C. The resulting mixture is allowed to warm up to room temperature. After 1 h, the reaction is quenched with 1 N HCl, and the solvent is evaporated under vacuum. The residue is taken up in CH2Cl2 and washed with brine, dried over anhydrous sodium sulfate. After concentration, the residue is purified with flash chromatography to the title compound (1.6 g, 70.5% yield for the two steps).

Workup

  1. customthe reaction is quenched with 1 N HCl
  2. customthe solvent is evaporated under vacuum
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue is purified with flash chromatography to the title compound (1.6 g, 70.5% yield for the two steps)

Sources & evidence

ORD record
ord-17a0bcc9469848e6a4a1258bd0f316a0
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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