2-Methoxy-5-nitrobenzoic acid → 5-Amino-2-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

Cycloartenyl ester of 2-methoxy-5-nitrobenzoic acid (34.0 g, 0.056 mole) prepared according to the procedure of Example 170 was suspended in acetic acid (1.2 l) at 20° C., and thereto 6N-HCl-dioxane (19 ml, 2 equivalent) and zinc powder (68 g) were added. The mixture was stirred at 30° C. for 1 hour. Then, zinc powder was removed by filtration, and the filtrate was concentrated under reduced pressure and the residue was extracted with chloroform. The chloroform extracts were washed successively with water and saturated aqueous NaHCO3 solution, then dried, concentrated, and the residual crystals were recrystallized from methylene chloride-hexane (1:4, v/v), giving cycloartenyl ester of 5-amino-2-methoxybenzoic acid (27.2 g) in a 84.4% yield. m.p. 180°-182° C.

Provenance & Evidence