Sulfuric Acid → 2-Amino-4,6-dimethoxybenzamide
Reaction equation
FC(F)(F)C(O)=[O:4].S(=O)(=O)(O)O.[NH2:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:15]=1[C:16]#[N:17].[OH-].[NH4+]>O>[NH2:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:15]=1[C:16]([NH2:17])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Trifluoroacetic acid (6.52 g, 4.4 mL) was charged to a flask equipped with a magnetic stirring bar and thermocouple. Sulfuric acid (96%, 9.2 g, 5 mL) was charged to the flask. In small portions 2-amino-4,6-dimethoxybenzonitrile (1.01 g, ˜76% pure) was charged to the mixed acid solution in the flask. A condenser was added and the solution was heated at 75° C. for 17 h. After the dark mixture had cooled to room temperature it was charged to water (9.79 g) cooled in a large ice bath while maintaining the reaction temperature below 10° C. Concentrated ammonium hydroxide (19.37 g) was added dropwise to the cooled solution (reaction temperature kept below 15° C.). The solution was then extracted two times with dichloromethane. The organic extracts were dried over MgSO4 and evaporated to yield the desired product (0.45 g) as a light brown solid.
Workup
- customequipped with a magnetic stirring bar
- additionA condenser was added
- temperatureAfter the dark mixture had cooled to room temperature it
- temperaturecooled in a large ice bath
- temperaturewhile maintaining the reaction temperature below 10° C
- extractionThe solution was then extracted two times with dichloromethane
- dry with materialThe organic extracts were dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-11505ce029344f69aacc27a9b1660d94
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346743B2
Reaction notes
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