Methylamine → 2-Amino-N-methylbenzamide

HRID 1487219Notes

Reaction equation

HRID 1487219 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 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isatoic anhydride (10 g, 61.3 mmol) was suspended in tetrahydrofuran (200 ml) and treated dropwise with methylamine in methanol (40%, 10 mL) with stirring. After stirring at room temperature for 16 hours, the solvent was distilled off under reduced pressure to afford the product 2-amino-N-methylbenzamide (9 g, yield 97.8%). 1H NMR (400 MHz, CDCl3) δ ppm 7.14-7.32 (m, 2H), 6.60-6.72 (m, 2H), 6.05 (br s, 1H), 2.97 (d, 3H, J=5.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-60c25448697a4550a50fc327ae96a48d
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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