Methanol → Methyl 6-chloropyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

An oven-dried, 500 milliliter (mL) round bottom flask (“RBF”) was charged with 6-chloronicotinic acid (compound 1) (14.4 grams (g), 91.3 millimole (mmol)), in 200 mL of freshly distilled MeOH. H2SO4 (1.22 mL, 22.8 mmol) was added dropwise to this mixture at room temperature. The mixture was stirred for 6 hours at 60° C. The organic phase was separated and extracted with ethyl acetate at pH 8. The organics were then combined and dried over Na2SO4. After filtering the mixture, the solvent was evaporated to obtain the crude product. The resulting crude product was then purified by silica gel column chromatography (eluent: methylene chloride:hexane=1:10 v/v) to yield 10.5 g (73%) of methyl 6-chloronicotinate (Compound 2).

Provenance & Evidence