HCID 21473553, compound → 2-amino-N,N,5-trimethylbenzamide
Reaction equation
[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-])=O>[Pd].C(O)C>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=1[C:3]([N:2]([CH3:15])[CH3:1])=[O:14]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of N,N,5-trimethyl-2-nitrobenzamide (11 g, 52.8 mmol) and 5% palladium on carbon (1 g) in 100 mL of ethanol was stirred under a hydrogen atmosphere for 18 hours. Additional 5% palladium on carbon (1 g) was added and the mixture was stirred for approximately 8 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified on silica gel by flash chromatography eluting with 4% ethanol/methylene chloride to give 2-amino-N,N,5-trimethylbenzamide (8 g, 44.9 mmol), m.p. 98°-99° C.