Methylamine → [2-(4-Chloro-2-nitrophenyl)ethyl](methyl)amine

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl amine in THF (2 M, 200 mL) was added 1-(2-bromo-ethyl)-4-chloro-2-nitro-benzene (17.5 g, 0.066 mole) in a pressure bottle, the reaction mixture was stirred at 60° C. overnight and the solvent was removed. The solid residue was treated with sodium hydroxide (1 N, 100 mL) and the aqueous extracted with methylene chloride (2×100 mL). The combined organic layers were washed with water (100 mL), saturated sodium chloride (100 mL), dried (sodium sulfate) and concentrated to provide 14.9 g of the title compound as a brown oil. 1H NMR (DMSO-d6): 7.95 δ (d, 1H); 7.67 δ (dd, 1H); 7.50 δ (t, 1H); 3.28 δ (broad, 1H); 2.85 δ (t, 2H); 2.64 δ (t, 2H); 2.20 δ (s, 3H).

Provenance & Evidence