Hydrochloric Acid → 4-(3,5-dimethylpyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 8-(cyclopropylmethoxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (1.1 g, 3.0 mmol) and conc. HCl (6 mL) was maintained at room temperature for 3 h and then cooled to 0° C. This cold solution was poured into a solution of 0.5 M pH 7 phosphate buffer (75 mL) and 10N NaOH (7.5 mL) at 0° C. The resulting mixture was stirred vigorously at 0° C. for 15 min, filtered, washed with water (0° C., 75 mL), and then dried under vacuum to give 0.92 g of 4-(3,5-dimethylpyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one. 1H NMR (400 MHz, DMSO-d6): δ 9.43 (s, 1H), 9.37 (s, 1H), 8.40 (s, 2H), 8.35 (s, 1H), 7.65 (d, 1H), 6.98 (d, 1H), 4.50 (s, 1H), 3.88 (s, 3H), 2.12 (s, 6H); MS (ESI): 312.6.

Provenance & Evidence