Sodium Hydroxide → 4-methylquinolin-3-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methyl-3-nitroquinoline (500 mg, 2.66 mmol) in conc. HCl (10 mL) was heated to 50° C. Tin (II) chloride dihydrate (1.5 g, 6.6 mmol) was added. The mixture was stirred at 50° C. overnight. The mixture was diluted with water (20 mL). The mixture was adjusted to pH 9 by addition of 5N aqueous sodium hydroxide. The mixture was cooled to 4° C. and extracted twice with ethyl acetate (30 mL). The combined extracts were washed with ice-cold water (40 mL) and dried over anhydrous Na2SO4, filtered, and concentrated to give 3-amino-4-methylquinoline (340 mg, 80%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 7.89-7.91 (m, 1H), 7.79-7.82 (m, 1H), 7.44-7.38 (m, 2H), 3.77 (br s, 2H), 2.37 (s, 3H).

Provenance & Evidence