4-Chloro-N1-methyl-N1-phenylbenzene-1,2-diamine synthesis

Yield:7485-22-5 87%

Reaction Conditions:

with tin(ll) chloride in ethanol at 40; for 6 h;

Steps:

76

4-Chloro-N'-methyl-N'-phenylbenzene-1. 2-diamine (Structure 63 of scheme XVI) To a solution of 4-chloro-N-methyl-2-nitro-N-phenylphenylamine (12.5 g, 46.3 mmol) in ethanol (250 mL) was added SnCl2. 2H20 (37.5 gr. , 0.17 mol). The solution was heated to 40°C and stirred for 6 h. The reaction mixture was concentrated in vacuo and subsequently diluted with ethyl acetate (500 mL) and washed with H20 (500 mL), a cooled (0°C) aq. solution of NaOH (1 M, 200 mL), H20 (500 mL) and brine (500 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced presssure. The crude compound was applied onto a silica column and eluted with heptane/ethyl acetate (8/2, v/v) affording the t itle compound (9.3 g, 87% yield). Data: Rf 0.65 (heptane/ethyl acetate, 7/3, v/v), (m/z) = 233 (M+H) +.

References:

WO2003/84963,2003,A1 Location in patent:Page/Page column 17; 62