Sodium Bicarbonate → 3-(1,3-Oxazol-2-yl)aniline

Participants

Reaction Conditions

Reaction Steps

To a slurry of stannous chloride dihydrate (11.8 g, 0.05 mol in 35 mL of ethyl acetate under argon at room temperature was added 2-(3-nitro-phenyl)1,3-oxazole (1.95 g, 0.01 mol, from part A). After heating at 80° C. for 20 minutes, the mixture was poured onto crushed ice and made basic (pH 8.5) with saturated sodium bicarbonate. After filtering the resulting solution through a pad of celite to remove insolubles, the organic layer was separated, washed with water and brine, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give 1.64 g of an oil that slowly solidified. 13C-NMR (CDCl3) δ162.1,146.8, 138.3, 129.7, 128.2, 117.0, 116.5, 112.5. m/s (m+H)+ @ 161; MW=160.

Provenance & Evidence