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

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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