3-NITROPHENETHYLAMINE HYDROCHLORIDE synthesis

Yield:-

Reaction Conditions:

with borane-THF in tetrahydrofuran at 20 - 70;

Steps:

A17
To a stirring solution of BH₃-THF (3.5 ml, 3.5 mmol, 1.0M) was added a solution of 2-(3-nitrophenyl)acetamide (0.25 g, 1.4 mmol) in THF (7.0 mL) at RT. The resulting solution was stirred at RT until the gas evolution had subsided and then heated at 70 °C overnight. The cooled reaction was quenched carefully with 3M HCl (2 ml)and heated again at 70 °C to complete the quench. The reaction was cooled to RT and concentrated to a white solid, which was dissolved in 3M NaOH (pH 14) and extracted with CH₂Cl₂ (4x). The organics were dried (Na₂SO₄), filtered, and concentrated to provide 0.20 g (87% yield) of crude product as an oil, which was purified by precipitation from CH₂Cl₂ and 3M HC1/EtOAc (0.26 ml, 0.78 mmol) to yield 2-(3-nitrophenyl)ethanamine as the HCl salt as an off-white solid (0.164 g).

References:

DECIPHERA PHARMACEUTICALS, LLC WO2006/71940, 2006, A2 Location in patent:Page/Page column 365