Cyanoacetamide → HCID 178426619, compound

Participants

Reaction Conditions

Reaction Steps

Acetic acid (7.93 mL) was treated sequentially with piperidine (13.6 mL), water (208 mL), 4-hydroxy-3-methylbut-3-en-2-one, sodium salt (31.7 g, 0.257 mol) then 2-cyanoacetamide (23.8 g, 0.283 mol) then heated to reflux for 6 hours. The reaction mixture was then cooled to <20° C., treated with acetic acid (28.3 mL), stirred for 10 minutes at 0° C., then filtered and washed with water (200 mL) to yield 2-hydroxy-5,6-dimethylnicotinonitrile. To the wet solid was added 6N hydrochloric acid (200 mL) and the mixture was heated to reflux for 3 days. The cooled reaction mixture was poured into ice-water and basified with concentrated ammonium hydroxide (200 mL) and stirred for 10 minutes. The mixture was filtered, washed with water and dried under vacuum at 60° C. to yield 5,6-dimethylpyridin-2-ol (9.57 g, 22%). 400 M Hz 1H NMR (DMSO-d6) δ: 11.19 (s, 1H), 7.19 (d, 1H), 6.04 (d, 1H), 2.09 (s, 3H), 1.91 (s, 3H).

Provenance & Evidence