Methylamine → 6-Chloro-N-methylnicotinamide

HRID 2399157Notes

Reaction equation

HRID 2399157 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 g 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-42e8dc0a7b3d4405ac4cb1f2ea71270b
Source dataset
uspto-grants-1977_05
Patent number
US04027027

Reaction notes

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