Acetic Acid → Methyl 2-chloro-6-methylpyridine-3-carboxylate

Participants

Reaction Steps

A 2 M ether solution of (trimethylsilyl)diazomethane (30 mL, 60.0 mmol) was added to a solution of 2-chloro-6-methylnicotinic acid (8 g, 45.2 mmol) in THF (100 mL) and MeOH (25 mL) in a room temperature water bath. After 30 min, HOAc (2 mL) was added. The mixture was concentrated and purified by silica gel chromatography, eluting with 0-20% EtOAc in hexanes, to give methyl 2-chloro-6-methylnicotinate as colorless oil (7.77 g, 93% yield). MS (ES+) m/z: 186 (M+H); LC retention time: 2.64 min (analytical HPLC Method A).

Provenance & Evidence