Sodium borohydride → HCID 10271065, compound

HRID 2356880Notes

Reaction equation

HRID 2356880 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:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[O:28])[CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[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:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][OH:28])[CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 9969824HCID 9969824, compound

Product 1

HCID 10271065HCID 10271065, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Cyanophenyl)-5-(2-pyridyl)-1-(3-formylphenyl)-1,2-dihydropyridin-2-one (585 mg) was dissolved in 20 ml of methanol, 260 mg of sodium borohydride were added with ice cooling and the mixture was stirred at room temperature for one night. The reaction solution was diluted with ethyl acetate, washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated in vacuo and purified by an NH silica gel column chromatography (ethyl acetate). The resulting crude crystals were recrystallized from ethyl acetate-diethyl ether to give 320 mg of the title compound.

Workup

  1. washwashed with a saturated saline solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. custompurified by an NH silica gel column chromatography (ethyl acetate)
  6. customThe resulting crude crystals were recrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-9044903a8860467e8263376aca21759a
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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