Methylamine → 32212-33-2

HRID 1688077Notes

Reaction equation

HRID 1688077 reaction equation
[CH3:1][N:2]1C(=O)O[C:5](=[O:6])[C:4]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:3]12.[CH3:14][NH2:15]>C1COCC1>[CH3:14][NH:15][C:5](=[O:6])[C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=1[NH:2][CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 25160N-Methylisatoic anhydride

Product 1

HCID 1093177832212-33-2

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methylisatoic anhydride (5 g, 28 mmol) in THF (100 mL) was treated with methylamine (THF solution, 2.0 M, 60 mL). The mixture was stirred for 18 h and the solvent was evaporated. The residue was partitioned between ethyl acetate (100 ml) and water (50 ml). The organic layer was washed once with brine (30 ml), dried over sodium sulfate, and concentrated to give N-methyl-2-methylamino-benzamide (5 g, 30 mmol): 1H NMR (300 MHz, CDCl3): δ 7.3 (m, 2H), 6.67 (d, 1H), 6.58 (t, 1H), 2.96 (d, 3H), 2.86 (d, 3H); MS (m/e) 165 (M+1).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between ethyl acetate (100 ml) and water (50 ml)
  3. washThe organic layer was washed once with brine (30 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-842a04a451b14fa4ab5081aa2403dc2d
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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