2-Propenoic acid, 3-(4-nitrophenyl)- → 3-(4-Aminophenyl)prop-2-enoic acid

Participants

Reaction Conditions

Reaction Steps

Cycloartenyl ester of p-nitro cinnamic acid (160.0 g, 0.266 mole) prepared according to the procedure of Example 101 was suspended in a mixture of acetic acid (1.5 l) and dioxane (1.5 l). To the suspension were added 6N-HCl-dioxane (95 ml) and zinc powder (80 g) and the mixture was stirred at 40° C. for 3 hours. After the reaction, zinc powder was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was extracted with chloroform. The extracts were washed successively with water and saturated aqueous NaHCO3, then dried, and concentrated under reduced pressure. The residual crystals were recrystallized from chloroform-ethanol (1:5, v/v), giving cycloartenyl ester of p-aminocinnamic acid (140.0 g), in a 92.0% yield. m.p. 185°-187° C.

Provenance & Evidence