Water → 2-Methylquinolin-6-amine

Participants

Reaction Steps

Tin(II) chloride dihydrate (60.4 g, 0.27 mol) and 2-methyl-6-nitroquinoline (8.4, 44.6 mmol) are stirred in ethanol and the mixture heated at reflux overnight. After cooling to room temperature, DI water (1.2 mL) is added and the solution made basic with sodium bicarbonate. The mixture is extracted with ethyl acetate (3×250 mL) and the combined organics dried (Na2SO4) and filtered. Solvent is evaporated to give a solid which is recrystallized from CH2Cl2 to give the title compound as crystals, 6.2 g (88%); mp187-189° C.; Anal. Calcd for C10H10 N2: C, 75.92; H, 6.37; N, 17.71. Found: C, 75.88; H, 6.35; N, 17.60.

Provenance & Evidence