Dimethyl 4-hydroxy-3-nitrophthalate → Dimethyl 3-amino-4-hydroxyphthalate

Participants

Reaction Steps

A mixture of the crude dimethyl 4-hydroxy-3-nitrophthalate C1-3 (25 g, 98 mmol) and Pd/C (1.0 g) in CH3OH (400 mL) was stirred at room temperature overnight under H2 atmosphere. LCMS showed that the reaction was complete. The reaction mixture was filtered through a celite pad and the filtrate was evaporated in vacuo. The residue was purified by chromatography (silica gel, PE:EA (1:1, v:v)) to yield compound C1-4 as a yellow solid (11.5 g, yield: 52%). 1H NMR (DMSO-d6, 400 MHz) δ: 10.45 (s, 1H), 6.89 (d, J=8 Hz, 1H), 6.37 (d, J=8 Hz, 1H), 5.19 (s, 2H), 3.75 (s, 3H), 3.72 (s, 3H); MS (ESI+): m/z 226 (M+1).

Provenance & Evidence