Methyl 2,4-dimethyl-3-nitrobenzoate → Methyl 3-amino-2,4-dimethylbenzoate
Reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([CH3:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[CH:9][C:10]=1[CH3:15])[C:4]([O:6][CH3:7])=[O:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of methyl 2,4-dimethyl-3-nitro-benzoate (37 g, 176.9 mmol) in methanol (370 mL), 10% palladium on carbon 50% wet (5.6 g) is added. The reaction is bubbled with hydrogen and placed under a hydrogen atmosphere for 6 days. The mixture is filtered through diatomaceous earth and the filtrate is evaporated to dryness. The resulting residue is purified by flash chromatography (silica gel), eluting with 20% ethyl acetate in hexanes to afford the title compound as a yellow oil (20.5 g, 65%). Mass spectrum (m/z): 180.1 (M+1). 1H NMR (300.16 MHz, DMSO-d6): δ 6.89 (s, 2H), 4.78 (s, 2H), 3.76 (s, 3H), 2.23 (s, 3H), 2.12 (s, 3H).