Hydrochloric Acid → HCID 20330424, compound

Participants

Reaction Steps

To a solution of 0.1 mole sodium ethoxide in 500 ml. of ethanol cooled to 10°-20° C. and under nitrogen is added 0.1 mole ethylisothiocyanate. The reaction mixture is stirred for 30 minutes after the addition is completed. There is then added portionwise 0.1 mole of 5-chloromethyl-2,2,8-trimethyl-4H-M-dioxino[4,5-C]pyridine. The reaction mixture is stirred at room temperature (or refluxed 3 hours) overnight, after which time 200 ml. of 6 N hydrochloric acid is added. The reaction mixture is stirred 5 hours at room temperature, concentrated in vacuo, and the residue taken up between benzene-ether (1:1) and excess saturated sodium bicarbonate. The organic layer is separated, washed well with water, dried and concentrated to give 2-methyl-3-hydroxy-4-hydroxymethyl-5-ethoxycarbonylthiomethylpyridine and hydrochloride salt.

Provenance & Evidence