Sodium Carbonate → Ethyl 2-bromo-5-methylpyridine-3-carboxylate

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Reaction Steps

The crude 2-cyano-5-(N,N-dimethylamino)-4-methyl-2,4-pentanedienoate (15.9 g) was dissolved in acetic acid (50 ml) and the mixture heated at 40°. A solution of 30% HBr/acetic acid (100 ml) was added dropwise and then the mixture was heated to 55° with stirring. After heating for 3/4 of an hour, the solution was poured onto ice, neutralized with solid Na2CO3 and extracted with CH2Cl2 (4×200 ml). The organic extracts were dried over Na2SO4, filtered and concentrated to dryness. The residue was distilled at 114°-120° (0.4 mm) to yield 6.3 g (35% yield) of ethyl 2-bromo-5-methylnicotinate.

Provenance & Evidence