(4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester → HCID 59253947, compound

Participants

Reaction Steps

(4-Nitro-phenoxy)-acetic acid methoxycarbonylmethyl ester 95 (20 grams, 74.3 mmol) was dissolved in dimethyl formamide (100 mL) in a pressure vessel, palladium on carbon (5%, 8 grams) added, and the mixture stirred under an atmosphere of H (4 Kg) for 2 hours. The catalyst was removed by filtration and to the filtrate; ice water (400 mL) was added. Crude 96 was extracted into ethyl acetate, dried over Na2SO4 and distilled, crude 3 was recrystallized from chloroform:hexane (1:6) to get pure 96 (13 grams, 73%) as a light brown shining powder. M.p: 76.5-78.5° C. IH NMR (CDCl3) δ 3.32(bs,2H,NH2), 3.76(s,3H,Ester), 4.70(s,2H,OCH2), 4.74(s,2H,OCH2), 6.60(d,2H,Ar), 6.74(d,2H,Ar).

Provenance & Evidence