Glycine → Methyl[1-(3-ethylphenyl)hydrazino]acetate

Participants

Reaction Steps

To the glycine (Intermediate 38; 35 g; 0.181 mol) in acetic acid (50 ml) at -5° C. was added, dropwise, a solution of sodium nitrite (13.75 g; 0.199 mol) in H2O (10 ml). The temperature of the reaction mixture was not allowed to rise above 0°. After stirring for a further 2 h, zinc dust (26.02 g, 0.398 mol) was added portionwise, once again so as not to allow the temperature of the reaction mixture to rise above 0°. After 5 h, a further quantity of zinc dust (13.01 g, 0.199 mol) was added and the mixture was stirred overnight. The excess zinc dust was removed by filtration through celite. The reaction mixture was then quenched with sodium bicarbonate solution. Extraction into ethyl acetate followed by washing with water, brine and finally drying (over Na2SO4) gave the crude title compound (ca. 35 g). This crude material was chromatographed using Ethyl acetate: Petroleum ether (1:3) to yield Intermediate 39 (5.21 g; 14%) as an oil.

Provenance & Evidence