5-Chloro-2-methylbenzonitrile → 5-Chloro-2-methylbenzylamine

Temperature

0 °C

A solution of 2-methyl-5-chlorobenzonitrile (2 g, 13.2 mmol), in THF (30 mL) was cooled to −15° C. and treated with 1 M lithium aluminum hydride in THF (13.4 mL). The reaction mixture was allowed to warm gradually to 0° C. over 2 h and was then stirred at room temperature for 1.5 h. It was then cooled to 0° C. and quenched sequentially with EtOAc (1 mL), water (0,5 mL), 15% NaOH (0.5 mL), and water (1.5 mL). After stirring for 1 h, the solids were removed via filtration. The filtrate was concentrated and the resulting residue purified by flash chromatography (98:2 methylene chloride/methanol) to give the product as an oil: 1H NMR (CDCl3) δ7.33 (d, J=2.0 Hz, 1H), 7.08 (m, 2H),, 3.83 (s, 2H),, 2.28 (s, 3H), 1.42 (br s, 2H).

1. temperatureIt was then cooled to 0° C.
2. customquenched sequentially with EtOAc (1 mL), water (0,5 mL), 15% NaOH (0.5 mL), and water (1.5 mL)
3. stirringAfter stirring for 1 h
4. customthe solids were removed via filtration
5. concentrationThe filtrate was concentrated
6. customthe resulting residue purified by flash chromatography (98:2 methylene chloride/methanol)

ORD record

ord-f4ae60e675734602a9c9c7704f2be6a1

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06387911B1