Acetic Acid → 2-amino-N,3-dimethylbenzamide

HRID 490978Notes

Reaction equation

HRID 490978 reaction equation
[CH3:1][C:2]1[C:11]2[NH:10]C(=O)[O:8][C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[CH3:18][NH2:19].O>C(OCC)(=O)C>[NH2:10][C:11]1[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:7]([NH:19][CH3:18])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6329Methylamine2×HCID 27598708-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 167706892-amino-N,3-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 8-methyl-2H-3,1-benzoxazine-2,4(1H)-dione (PCT Patent Publication WO 00/27831) (18 g, 0.1 mol) and acetic acid (1.2 g, 0.02 mol) in ethyl acetate (200 mL) was warmed to 35° C., and aqueous methylamine (40%, 9.0 g, 0.12 mol) was added dropwise over 50 minutes at 35-37° C. Then more aqueous methylamine (40%, 0.9 g, 12 mmol) was added, and the mixture was stirred an additional 2.5 h at 36° C. Then water (20 mL) was added, the layers were separated, and the organic layer was washed with water, dried (MgSO4), and evaporated to afford the title compound, 15.45 g (92%).

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-63d313d19e614a4b84c26412ebcc2b8e
Source dataset
uspto-grants-2009_05
Patent number
US07528260B2

Reaction notes

Loading…