(3-chloro-5-methoxyphenyl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 3-chloro-5-methoxybenzylamine (4.6 mmol, 0.792 g) in DCM (anhydrous, 20 ml) was cooled to −78° C. and BBr3 (1 M in DCM, 9.43 mmol) was added dropwise. The reaction was allowed to reach room temperature over night with stirring. The reaction was quenched by careful addition of methanol (5 ml), solvents were evaporated under reduced pressure and the residue was purified by means of chromatography (silica, DCM/MeOH/NH3 (30% in water) Sep. 1, 2001 v/v/v) to provide the title compound (0.48 g, 66%) as a white solid. (DMSO, 500 MHz) δ 3.61 (s, 2H), 4.57 (br, 1H), 6.62 (s, 1H), 6.80 (s, 1H) and 6.83 (s, 1H). to reach room temperature over night The reaction was quenched by careful addition of methanol (5 ml), solvents were evaporated under reduced pressure the residue was purified by means of chromatography (silica, DCM/MeOH/NH3 (30% in water) Sep. 1, 2001 v/v/v)

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

Procedure: A solution of 3-chloro-5-methoxybenzylazide (5 mmol, 0.988 g) in THF (20 ml) was cooled to −78° C. and LiAlH4 (1 M, 7.5 mmol, 7.5 ml) was added dropwise with stirring. After 30 min the reaction was allowed to reach 0° C. and the mixture was stirred for another 1 h. To the resulting sharp yellow solution was added ethyl acetate (0.3 ml), followed by water (0.3 ml), NaOH (15% w/w in water) and water (0.9 ml). The resulting mixture was filtered and the solids washed with acetonitrile (15 ml). The solvents were evaporated off to provide the title compound (0.792 g, 92%) as a clear, colorless liquid. The product was used in the next step without further purification. An analytical pure sample was obtained by means of flash chromatography (silica, DCM/MeOH/NH3 (30%) 97/3/0.3 v/v/v). 1H NMR (CDCl3, 500 MHz) δ 1.46 (br, 2H), 3.77 (s, 3H), 3.79 (s, 2H), 6.74 (s, 1H), 6.75 (S, 1H) and 6.87 (s, 1H). to reach 0° C. the mixture was stirred for another 1 h The resulting mixture was filtered the solids washed with acetonitrile (15 ml) The solvents were evaporated off