Hydrochloric Acid → 2-Methylpyridine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a mechanically (overhead) stirred solution of 2,4-lutidine (140 g, 1.31 mol) in water (1500 mL) was added KMnO4 (412 g, 2.61 mol) portion-wise at 80° C. over a period of 3 h, taking care to allow each portion to react before adding the next. The reaction mixture was then stirred at 80° C. for overnight. The solution was allowed to settle and the aqueous layer separated from the precipitated MnO2. The water was then removed under reduced pressure to produce a volume of approximately 400 mL. Remaining water was chilled in an ice bath and acidified to pH 3.0 with dilute HCl. Solid was allowed to precipitate for an addition hour, then filtered and dried under high vacuum at 50° C. for 48 h to give white solid product (54.9 g, 30% yield).

Provenance & Evidence