Isatoic Anhydride → 2-amino-N-methoxy-N-methylbenzamide
Reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.[C:13]12[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:18]C(=O)[O:16][C:14]2=O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:5][O:4][N:3]([CH3:2])[C:14](=[O:16])[C:13]1[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of N,O-dimethylhydroxylamine hydrochloride (51.2 g, 0.53 mmol) in 90-95% aqueous ethanol (200 ml) is added triethylamine (53 g, 0.53 mmol) and, after 10 minutes stirring at 25° C., isatoic anhydride (37.0 g, 0.35 mmol) in portions. The reaction is then heated at reflux for 1.5 hrs and poured onto an equal volume of ice and saturated sodium bicarbonate. The ethanol is then removed by rotary evaporation, the resulting aqueous mixture extracted with ethyl acetate (3×150 ml), the combined extracts washed with water, brine, dried over magnesium sulfate and activated charcoal, and concentrated to an orange oil. The oil is chromatographed on silica gel (1:1 diethyl ether: hexanes, then acetone) and distilled to give N-methoxy-N-methyl anthranilic acid amide as a pale yellow oil; yield 47.4 g (75%); b.p. 148°-151° C./0.35 mm.
Workup
- temperatureThe reaction is then heated
- temperatureat reflux for 1.5 hrs
- customThe ethanol is then removed by rotary evaporation
- extractionthe resulting aqueous mixture extracted with ethyl acetate (3×150 ml)
- washthe combined extracts washed with water, brine
- dry with materialdried over magnesium sulfate and activated charcoal
- concentrationconcentrated to an orange oil
- customThe oil is chromatographed on silica gel (1:1 diethyl ether
- distillationhexanes, then acetone) and distilled
Sources & evidence
- ORD record
- ord-d62ba144fbe64b0a8f517137cabcb8f8
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05136085
Reaction notes
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