Ammonia → 1-[5-Chloro-2-(methylsulfonyl)phenyl]methanamine hydrochloride

(Step 3) To a solution of 5-chloro-2-(methylsulfonyl)benzonitrile obtained in Step 2 (3.8 g) in ethanol (25 ml) was added an 8N solution of ammonia in methanol (5 ml) and Raney cobalt (19 g, wet). The resulting mixture was stirred overnight at room temperature under a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. To the residue were added ethanol (10 ml) and a 2 M hydrogen chloride-methanol solution (10 ml). The resulting mixture was concentrated under reduced pressure, and the residual solid was collected by filtration and washed with ethyl acetate to give 1-[5-chloro-2-(methylsulfonyl)phenyl]methanamine hydrochloride (3.6 g) as a white solid.

1. filtrationThe reaction mixture was filtered through celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionTo the residue were added ethanol (10 ml)
4. concentrationThe resulting mixture was concentrated under reduced pressure
5. filtrationthe residual solid was collected by filtration
6. washwashed with ethyl acetate

ORD record

ord-270105f4d07f46679a2d137839392f93

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481569B2