4-Chloroaniline → HCID 178512017, compound

Trimethylaluminum (2 M in hexanes, 100 ml, 200 mmol) was added dropwise to a solution of 4-chloro-phenylamine (18.2 g, 143 mmol) in toluene (550 ml) under a N2 atmosphere at 0° C. The reaction mixture was warmed to room temperature and stirred for 3.5 hours. A solution of 2-chlorobenzonitrile (23.6 g, 171 mmol) in toluene (140 ml) was added and the reaction mixture was heated at 80° C. for 17 hours, during which time it became homogeneous. The reaction mixture was then cooled to room temperature and poured over a slurry of silica gel in CHCl3/methanol (2:1). After filtration, the filter cake was washed with a mixture of CH2Cl2/MeOH (2:1). The combined filtrates were concentrated in vacuo, and the solid yellow residue was triturated with hexanes/ether (2:1). The product I-5a (25.1 g, 66%) was used in the next reaction without further purification.

1. temperaturethe reaction mixture was heated at 80° C. for 17 hours, during which time it
2. temperatureThe reaction mixture was then cooled to room temperature
3. filtrationAfter filtration
4. washthe filter cake was washed with a mixture of CH2Cl2/MeOH (2:1)
5. concentrationThe combined filtrates were concentrated in vacuo
6. customthe solid yellow residue was triturated with hexanes/ether (2:1)
7. customThe product I-5a (25.1 g, 66%) was used in the next reaction without further purification

ORD record

ord-8a4815bc45884661bf9dd6f3a64844c2

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07145012B2