Water → 4-Chloro-N-methylpicolinamide

HRID 404710Notes

Reaction equation

HRID 404710 reaction equation
O.[OH-].[Na+].Cl.[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][CH3:15])=[O:13])[CH:7]=1>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][CH3:15])=[O:13])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 467810064-Chloro-N-methylpyridine-2-carboxamide--hydrogen chloride (1/1)

Product 1

HCID 14768144-Chloro-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A reaction flask with stirrer was charged with 41.4 g of 4-chloro-N-methyl-pyridine-2-carboxamide hydrochloride and 100 g of toluene as solvent. After addition of 68.4 g of water and 19.6 g of an aqueous sodium hydroxide solution (45% w/w) the reaction mixture was stirred for 30 minutes. The two phases were separated and the aqueous layer was discarded. The organic layer was concentrated by distillation under vacuum and toluene was substituted by 1-methyl-2-pyrrolidinone (70 g) to yield a solution of 4-chloro-N-methyl-pyridine-2-carboxamide in 1-methyl-2-pyrrolidinone.

Workup

  1. customThe two phases were separated
  2. concentrationThe organic layer was concentrated by distillation under vacuum and toluene

Sources & evidence

ORD record
ord-1d00d96d1a524cc38e921925625c88c7
Source dataset
uspto-grants-2014_06
Patent number
US08748622B2

Reaction notes

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