Hydrochloric Acid → 4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium

Participants

Reaction Conditions

Reaction Steps

2,3,5-trimethyl-4-nitropyridine 1-oxide (850 g, 4.67 mol) was charged with water (400 g) and 36% concentrated hydrochloric acid (1.69 kg), and the resultant solution was heated to 70° C. The solution was then charged with N,N-dimethylformamide (115 mL) and heated to 100° C. Once the reaction had finished, the solution was cooled to 20° C. and then charged into a mixture of potassium carbonate (1.40 kg) and water (7 L). The resultant mixture was extracted with chloroform (1.0 L×3), dried over sodium sulfate and then concentrated. The resultant crude product was stirred for 2 hours in a mixed solution of diisopropyl ether (500 mL) and n-hexane (1.0 L), and the resultant solution was then filtered with suction. The resultant wet substance was dried overnight under vacuum to obtain 666.4 q of the title compound.

Provenance & Evidence