Ammonium Hydroxide → 2-Amino-5-methoxybenzamide

HRID 1014164

Reaction equation

HRID 1014164 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11]C(=O)[O:9][C:8](=O)[C:7]=2[CH:14]=1.[OH-].[NH4+:16]>C(OCC)(=O)C>[NH2:11][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]=1[C:8]([NH2:16])=[O:9]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 203382172-Amino-5-methoxybenzamideYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione (3.0 g, 16 mmol, Trans World Chemicals) was treated directly with 27% aqueous ammonium hydroxide. After one hour the organic phase was diluted with ethyl acetate, washed twice with aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried over sodium sulfate. Filtration and removal of the residual solvent gave 2-amino-5-(methyloxy)benzamide as a white solid (1.42 g, 53% Yield);. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.63 (s, 3 H), 6.07 (s, 2 H), 6.60 (d, J=8.97 Hz, 1 H), 6.79 (dd, J=8.79, 2.93 Hz, 1 H), 7.03 (s, 1 H), 7.06 (d, J=2.93 Hz, 1 H), 7.71 (s, 1 H).

Workup

  1. washwashed twice with aqueous sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration and removal of the residual solvent

Sources & evidence

ORD record
ord-c1e55b81dead4a81bbf7f7967a06e27a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Linked notes

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