Methylamine → 32212-33-2

HRID 1041735Notes

Reaction equation

HRID 1041735 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-c40d4481400249b28fce57393b4d2b07
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…