Ammonia → 2-Chloro-4-methylpyridine-3-carboxamide

HRID 2396584Notes

Reaction equation

HRID 2396584 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.O=S(Cl)Cl.[NH3:16]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]([NH2:16])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 154837662-Chloro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 109428862-Chloro-4-methylpyridine-3-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-chloro-4-methyl-3-pyridinecarboxylic acid (24.7 g, 157 mmol) and 75 mL of toluene at 70° C. was added 75 mL of SOCl2 (22.6 g, 190 mmol) within a period of 1 hour. The reaction mixture was refluxed for 4 hours and the resulting solution was cooled to room temperature. Dry NH3 gas was introduced at such a rate so as to maintain the internal temperature below 30° C. After removing toluene, the solid residue was washed successively with cold water and methanol, and dried to yield 22.72 g of the title compound (91%, m.p. 168°-170° C.).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. temperatureto maintain the internal temperature below 30° C
  3. customAfter removing toluene
  4. washthe solid residue was washed successively with cold water and methanol
  5. customdried

Sources & evidence

ORD record
ord-7153c737860b4ca2803911bb6ce5a8eb
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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