Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate → Methyl 3-amino-5-[(dipropylamino)carbonyl]Benzoate
Reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:6])[CH2:2][CH3:3]>[Pd].CO>[NH2:17][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:20][CH2:21][CH3:22])=[O:6])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate (XXX, PREPARATION 9, 6.00 g, 20.0 mmol) and palladium on carbon (5%, 0.600 g) in methanol (40 mL) is shaken in a hydrogenation apparatus under hydrogen (45 psi) for 3 hours. The mixture is then filtered through diatomaceous earth and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 7.27, 6.77, 4.10, 3.82, 3.38, 3.10, 1.62, 1.46, 0.91 and 0.68.