Benzyl Bromide → HCID 10445614, compound

HRID 2081539Notes

Reaction equation

HRID 2081539 reaction equation
[C:1]([C:3]1[C:4](=[O:13])[NH:5][C:6]([CH3:12])=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1)#[N:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:14]([O:13][C:4]1[C:3]([C:1]#[N:2])=[CH:8][C:7]([C:9](=[O:11])[CH3:10])=[C:6]([CH3:12])[N:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 27654765-Acetyl-2-hydroxy-6-methylnicotinonitrile

Product 1

HCID 10445614HCID 10445614, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 3-cyano-5-acetyl-6-methyl-2(1H)-pyridinone (1.76 g, 0.01 mol) (L. Mosti et al, J. Het. Chem. 22, 1503 (1985)), benzyl bromide (2.12 g, 0.012 mol), silver carbonate (3.06 g, 0.011 mol) in benzene was stirred at room temperature under a nitrogen atmosphere overnight, while protected from light. The following day the mixture was filtered, and the solids washed well with benzene. Evaporation of the filtrate gave the desired intermediate, mp 94°-99° C.

Workup

  1. filtrationThe following day the mixture was filtered
  2. washthe solids washed well with benzene
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-991ed8f284b14acfa0eff7d6af92beff
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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