Sodium Methoxide → HCID 19829820, compound

Participants

Reaction Steps

To a solution of methyl [2-[aminocarbonyl]-1-[4-methoxy-3-methyl phenyl]hydrazino]acetate (Intermediate 98, 222 mg, 0.8 mmol) in methanol (5 ml) was added sodium methoxide (43 mg, 0.8 mmol) with stirring and under nitrogen. After 30 minutes further sodium methoxide (43 mg, 0.8 mmol) was added and the reaction stirred at room temperature for 14 hours. Three separate portions of sodium methoxide (43 mg, 0.8 mmol) were then added with 30 minutes between each before the reaction was poured into pH 6 buffer (30 ml) and extracted with ethyl acetate (2×25 ml). The organic extract was dried (MgSO4) and evaporated to give a white semi-solid which was triturated with ethylacetate-ether (~1:1) to give an off white solid. This was dissolved in ethyl acetate (10 ml), filtered and evaporated to give the title compound as an off white solid (18 mg, 10%) m.p. 220°-222° C. (decomp).

Provenance & Evidence