Ethyl Acetate → 1-(3-Chloro-5-methoxyphenyl)methanamine

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).

1. customto reach 0° C.
2. stirringthe mixture was stirred for another 1 h
3. filtrationThe resulting mixture was filtered
4. washthe solids washed with acetonitrile (15 ml)
5. customThe solvents were evaporated off

ORD record

ord-4c5f6104900a4bd08741441c589abc51

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799947B2