Sodium Dithionite → 2-Amino-4-(benzyloxy)-3-methoxybenzoic acid

Participants

Reaction Steps

To a vigorously stirring suspension of 4-benzyloxy-3-methoxy-2-nitrobenzoic acid (10.918 g, 0.036 mol) in water (200 ml) containing sodium acetate trihydrate (4.5 g) was added portionwise of sodium hydrosulfite (31 g, 0.18 mol) for 2 hours at 70 ° C. The reaction mixture was kept at this temperature for an additional 4 hours. After cooling, the precipitates were collected by filtration and washed with water. The product was recrystallized from ethanol to give 4-benzyloxy-3-methoxyanthranilic acid, 6.46 g (65.6%) with mp. 167-8 ° C. 1H-NMR: Analyses: Calculated for C15H15NO4 : C, 65.92; H, 5.53; N, 5.13. Found: C, 66.14; H, 5.55; N, 5.24.

Provenance & Evidence