Isopropanol → 6-[(Propan-2-yl)oxy]pyridine-3-carboxylic acid

Participants

Reaction Steps

To a solution of potassium tert-butoxide (0.891 g, 7.94 mmol) in tetrahydrofuran (40 mL) at 0° C. was isopropanol (0.608 mL, 7.94 mmol) added. 6-chloronicotinonitrile (1.0 g, 7.22 mmol) was added after stirring for 5 min and the reaction mixture was allowed to reach ambient temperature. The reaction mixture was concentrated in vacuo, water (50 mL) was added and the resulting mixture extracted with ethyl acetate (3×50 mL). The crude was suspended in 4M sodium hydroxide (30 mL) and heated to reflux over night. The reaction mixture was concentrated in vacuo and 1M hydrochloric acid was added until an acidic pH was reached. The formed precipitate was collected by filtration and washed with water to yield 1.140 g (85%) of the title compound; 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (s, 1 H), 8.70 (d, 1 H), 8.10 (dd, 1 H), 6.82 (d, 1 H), 5.21-5.40 (m, 1 H), 1.31 (d, 6 H); MS (ESI) m/z 182[M+H+].

Provenance & Evidence