T. Voronina, I. Rakhmankulova, O. Rudenko
2004
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Journal
Pharmaceutical Chemistry Journal
Abstract
Methyl N-(2-Oxy-5-bromobenzhydry!)glycine (I). A 0.69 g (0.01 mole) portion of NaNO 2 in 5 ml of water was added over a period of 5 to 6 min at 0-2~ to a solution of 3.49 g (0.01 mole) of methyl N-(2-oxy-5-bromobenzhydryl)glycine [5] in 20 ml of 18% HCI after which the mixture was stirred for 15-16 min. The mixture was then heated at 35-40~ for 1.5-2 h. The separated oil was removed. A 50 ml portion of water was added to the oil which was heated at 90-95~ until the evolution of gas halted. The mixture was then cooled to 10-15~ neutralized with 5-10% NaHCO 3. A 60 ml portion of diethyl ether was added to the mixture, the ether solution was separated, washed with water (3 • 20 ml), dehydrated with Na2SO 4, evaporated, and the residue was crystallized from MeOH. Yield of compound I was 0.74 g (21%), mp 92-93~ Rf 0.39. C16HI6BrNO S. IR-spectrum, Vmax: 1740 cm -I (C = O).