4-Chloropyridine-2-carboxylic acid → HCID 21076072, compound

Participants

Reaction Conditions

Reaction Steps

Sodium bis(trimethylsilyl)amide (28.8 g, 157 mmol) was added slowly to anhydrous n-butanol (52 mL). After 1 h, 4-chloro-pyridine-2-carboxylic acid (3.00 g, 19.1 mmol) was added and the reaction was heated to 150° C. for 3 h. Potassium bis(trimethylsilyl)amide (7.80 g, 39.2 mmol) in n-butanol (30 mL) was added to the reaction mixture and this was heated o.n. The mixture was cooled to r.t and pH was adjusted to 5 with 1N NaHSO4 solution. The mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered and the solvent was removed in vacuo to give the title compound (3.40 g, 94% yield) as a solid.

Provenance & Evidence