Sodium Bicarbonate → 2-Amino-5-methoxy-4-nitrobenzamide
Reaction equation
[CH3:1][O:2][C:3]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:6]2[NH:7]C(=O)[O:9][C:10](=O)[C:5]=2[CH:4]=1.C([O-])(=O)C.[NH4+:22].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[NH2:7][C:6]1[CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:10]([NH2:22])=[O:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
476 mg (2 mmol) of 6-methoxy-7-nitro-1H-benzo[d][1,3]oxazine-2,4-dione and 1.5 g (20 mmol) of ammonium acetate were dissolved in 20 ml of acetic acid and heated at 105° C. for 3 hours. The reaction mixture was then poured into ice-water and slowly brought to pH 7 with solid sodium bicarbonate. The aqueous phase was extracted with ethyl acetate. The organic phase was washed with water, dried and concentrated in vacuo. The crude product was triturated with diethyl ether, and the resulting precipitate was filtered off with suction. 285 mg (68%) of the desired product were obtained.
Workup
- extractionThe aqueous phase was extracted with ethyl acetate
- washThe organic phase was washed with water
- customdried
- concentrationconcentrated in vacuo
- customThe crude product was triturated with diethyl ether
- filtrationthe resulting precipitate was filtered off with suction
Sources & evidence
- ORD record
- ord-624e83a88f9746d187df97d194ed269b
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247452B2
Reaction notes
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