Methyl 3-methoxy-4-nitrobenzoate → Methyl 4-amino-3-methoxybenzoate

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:6]([O:8][CH3:9])=[O:7]>CCO.C1COCC1.[Pd]>[NH2:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Komponenten

Versuchsvorschrift

A stirred mixture of methyl 3-methoxy-4-nitrobenzoate (1.20 g, 5.7 mmol) and 5% Pd-C (1.0 g) in EtOH (30 mL) and THF (20 mL) was hydrogenated overnight at 1 atm. The mixture was filtered and the filtrate was evaporated. The residue was chromatographed on silica-gel with CHCl3 as eluent, and the solid obtained was further purified by recrystallization from CHCl3-n-hexane to give 805 mg (78%) methyl 4-amino-3-methoxybenzoate as white plates. mp 126-128; IR (KBr) 3475, 1700 cm−1; 1H-NMR (CDCl3) δ3.86 (3H, s), 3.89 (3H, s), 4.21 (2H, br s), 6.66 (1H, d, J=8.3 Hz), 7.45 (1H, d, J=1.9 Hz), 7.54 (1H, dd, J=1.9 and 8.3 Hz); MS (FAB) m/z 182 (M++1); Anal. Calcd. for C9H11NO3: C, 59.66; H, 6.12; N, 7.73. Found: C, 59.65; H, 6.15; N, 7.65.