4-chloro-2-N-methylbenzene-1,2-diamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-chloro-N1-methylbenzene-1,2-diamine (383 mg, 2.446 mmol) and 4-diethoxymethyl-pyridine-3-carbaldehyde (512 mg, 2.446 mmol) in 1,4-dioxane (20 mL) was heated to 75° C. overnight. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel flash chromatography employing heptane-ethyl acetate (1:1) to give of 6-chloro-2-(4-diethoxymethyl-pyridin-3-yl)-1-methyl-1H-benzoimidazole. concentrated in vacuo The residue was purified by silica gel flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-chloro-N2-methyl-benzene-1,2-diamine (60) (100 mg, 0.64 mmol, 1 eq), triphosgene (95 mg, 0.32 mmol, 0.5 eq), TEA (0.26 ml) in THF (2 ml) was stirred at rt for 4 hours. The reaction solution was washed with ethyl acetate and concentrated to provide 6-chloro-1-methyl-1,3-dihydro-benzoimidazol-2-one (61). The reaction solution was washed with ethyl acetate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (5-chloro-2-nitro-phenyl)-methyl-amine (59) (500 mg, 2.7 mmol, 1 eq), SnCl2.2H2O (3.0 g, 13.3 mmol, 5 eq) in ethyl acetate (25 ml) was refluxed overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated potassium carbonate solution. The organic phase was concentrated and the crude residue was purified with flash chromatography to give 4-chloro-N2-methyl-benzene-1,2-diamine (60). was refluxed overnight washed with saturated potassium carbonate solution The organic phase was concentrated the crude residue was purified with flash chromatography