Ethanol → 4-Chloro-N-methylpyridine-2-carboxamide--hydrogen chloride (1/1)

HRID 404709Notes

Reaction equation

HRID 404709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH3:11])=[O:9])[CH:3]=1.C(O)C.C(Cl)(=O)C>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH3:11])=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 14768144-Chloro-N-methylpicolinamide

Product 1

HCID 467810064-Chloro-N-methylpyridine-2-carboxamide--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

420 g of a solution of 4-chloro-N-methylpyridine-2-carboxamide (prepared according to WO2006/034796) in toluene (approx. 30% w/w) and 48.8 g of ethanol were charged into a reaction flask. 67.2 g of acetyl chloride was added with stirring to such a degree that the temperature of the reaction mixture did not exceed 30° C. After stirring further at room temperature for 1.5 h the product was filtered off, washed with toluene (212 g) and dried under reduced pressure (30° C., 80 mbar). In this way 156 g (quantitative yield) of 4-chloro-N-methyl-pyridine-2-carboxamide hydrochloride were obtained.

Workup

  1. customdid not exceed 30° C
  2. stirringAfter stirring further at room temperature for 1.5 h the product
  3. filtrationwas filtered off
  4. washwashed with toluene (212 g)
  5. customdried under reduced pressure (30° C., 80 mbar)

Sources & evidence

ORD record
ord-1009b61a810a402e9d578a174dfa6686
Source dataset
uspto-grants-2014_06
Patent number
US08748622B2

Reaction notes

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