Sodium borohydride → HCID 10271065, compound

HRID 547697Notes

Reaction equation

HRID 547697 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-6e129fe4f2134a6b8f45d05c350aa533
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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