Methanol → 3-(2-Cyanophenyl)-5-(alpha-hydroxy-2-picolyl)-1-phenyl-1,2-dihydropyridin-2-one

HRID 547738Notes

Reaction equation

HRID 547738 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:29])[N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:12]=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=O)[CH:14]=1)#[N:2].[BH4-].[Na+].C[OH:33]>C(=O)([O-])O.[Na+]>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:29])[N:11]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]([CH2:15][C:17]2([OH:33])[CH:22]=[CH:21][CH:20]=[CH:19][NH:18]2)[CH:14]=1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 223190923-(2-Cyanophenyl)-5-(2-pyridinecarbonyl)-1-phenyl-1,2-dihydropyridin-2-one

Product 1

HCID 865910463-(2-Cyanophenyl)-5-(alpha-hydroxy-2-picolyl)-1-phenyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 25 mg of 3-(2-cyanophenyl)-5-(2-pyridinecarbonyl)-1-phenyl-1,2-dihydropyridin-2-one in 5 ml of methanol was added 2 mg of sodium borohydride under ice-cooling. After 30 minutes, the mixture was diluted with a saturated aqueous solution of sodium hydrogen carbonate, followed by extracting with ethyl acetate. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate), to give 15 mg of the title compound as a pale yellow powder.

Workup

  1. temperaturecooling
  2. extractionby extracting with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-82a33880e1b74a19850f735a7ce6f719
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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