Methylamine → 2-Amino-N-methylbenzamide

HRID 2187054Notes

Reaction equation

HRID 2187054 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)O[C:2]2=[O:3].[CH3:13][NH2:14]>O1CCCC1.CO>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:14][CH3:13])=[O:3]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 8359Isatoic Anhydride

Product 1

HCID 3080722-Amino-N-methylbenzamideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isatoic anhydride (10.0 g) was suspended in tetrahydrofuran (200 ml) and treated dropwise with 40% solution of methylamine in methanol (10.0 ml) with stirring. After stirring at room temperature for 16 hours, the solvent was distilled off under reduced pressure to give the title compound (10.3 g, about 100%). Melting point: 78.0 to 79.0° C. (recrystallized from ethyl acetate-n-hexane).

Workup

  1. stirringAfter stirring at room temperature for 16 hours
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a2afcf653be646b99593fb5270f424aa
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

Loading…