Methylamine → 2-amino-N,3-dimethylbenzamide

HRID 2422571Notes

Reaction equation

HRID 2422571 reaction equation
[CH3:1][C:2]1[C:3]([NH2:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].[CH3:12][NH2:13]>C1COCC1>[NH2:11][C:3]1[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH:13][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 781012-Amino-3-methylbenzoic acid

Product 1

HCID 167706892-amino-N,3-dimethylbenzamideYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methyl-2-aminobenzoic acid (3.43 g, 22.7 mmol) and N,N′-carbonyldiimidazole (4.05 g, 24.9 mmol) were stirred in THF at 40° C. for 3 hours. After cooled to room temperature, methylamine (2.0 M in THF, 22.7 ml) was added thereto, and further stirred for 1 hour at room temperature. The solvent was evaporated off under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform/methanol=9/1) to obtain the intended compound (3.43 g, yield 92%) as a milky white solid.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue was purified through silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-ad85cc1100664fecad6b8dab39d20c97
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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