Methylamine → 6-Chloro-N-methylnicotinamide

HRID 1390656Notes

Reaction equation

HRID 1390656 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[CH3:11][NH2:12]>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:11][NH:12][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 123642306-Chloro-N-methylnicotinamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

26.2 of crude 6-chloro-nicotinic acid chloride are introduced in portions into a solution of 25 ml of anhydrous methylamine in a mixture of 150 ml of dioxane and 50 ml of toluene whilst cooling at 0° C. to -5° C., and the mixture is then stirred for 3 hours longer, without further cooling. The reaction mixture is evaporated in vacuo, the residue is stirred with 100 ml of water and the undissolved material is filtered off and dried, giving crude 6-chloro-nicotinic acid N-methylamide of melting point 150°-154° C.

Workup

  1. temperaturewhilst cooling at 0° C. to -5° C.
  2. customThe reaction mixture is evaporated in vacuo
  3. stirringthe residue is stirred with 100 ml of water
  4. filtrationthe undissolved material is filtered off
  5. customdried

Sources & evidence

ORD record
ord-c1239eb3fa534cf3b148dd6db95b3034
Source dataset
uspto-grants-1979_02
Patent number
US04139623

Reaction notes

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