Methane → Glycinamide

Participants

Reaction Steps

An aqueous solution of glycinamide (0.027 mol, 3.03 g), which was prepared by neutralizing glycinamide hydrochloride with one equivalent of 10N NaOH, was slowly added to a stirring solution of 2-fluoro-5-methoxyphenyl glyoxal (0.027 mol, 5.42 g) in MeOH (35 mL) at 0° C. One equivalent of 10N NaOH (2.74 mL) was then added slowly to the resulting clear orange solution. After stirring overnight at room temperature the solution was acidified to pH~3 with 12N HCl and the methanol was evaporated under reduced pressure. The residue was partitioned between CH2Cl2 and water and the aqueous phase was extracted (5×) with CH2Cl2. The combined CH2Cl2 portions were dried (Na2SO4) and concentrated under reduced pressure to give a dark solid. The solid was dissolved in CH2Cl2/MeOH, heated for five minutes with decolorizing charcoal and filtered through 2 inches of silica gel (5% MeOH/CH2Cl2 eluent). Evaporation of the solvents under reduced pressure afforded 5-(2-fluoro-5-methoxyphenyl)-pyrazin-2-one.

Provenance & Evidence