Sodium Hydroxide → 2-Methylquinolin-3-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-3-nitroquinoline (400 mg, 2.13 mmol) in conc. HCl (8 mL) was heated to 50° C. Tin (II) chloride dihydrate (1.2 g, 5.3 mmol) was added. The mixture was stirred at 50° C. overnight. The mixture was diluted with water (20 mL). The pH was brought to 9 by addition of aqueous 5 N NaOH. The mixture was cooled to 4° C. and extracted with ethyl acetate (2×30 mL). The combined extracts were washed with ice-cold water (40 mL) and dried over anhydrous Na2SO4, filtered, and concentrated to give 3-amino-2-methylquinoine (270 mg, 80%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.84 (d, J=8.4 Hz, 1H), 7.51 (dd, J=1.2, 8.0 Hz, 1H), 7.39-7.30 (m, 2H), 7.16 (s, 1H), 3.77 (s, 2H), 2.56 (s, 3H).

Provenance & Evidence