Isopropylamine → 2-{[(Propan-2-yl)amino]methyl}aniline

Participants

Reaction Steps

To a 500 ml 3-necked round bottom flask equipped with overhead mechanical stirrer, thermometer and nitrogen bubbler was charged 2-nitrobenzaldehyde (200 g, 1.32 mol) in methanol (1300 ml), to which was added isopropylamine (78.0 g, 113 ml, 1.32 mol) in one portion with stirring under nitrogen. The reaction mixture was then stirred for 100 minutes (followed reaction by GC), then added to a 4 litre stainless steel Parr hydrogenator, containing a suspension of 5% palladium on charcoal (13.24 g, 6% cat. loading) in methanol (500 ml) and the suspension hydrogenated under hydrogen at 60 psi for 3 hours. The suspension was filtered through a pad of celite, the pad washed with methanol (500 ml) and the combined filtrate evaporated under reduced pressure to leave a yellow oil, 2-amino-N-(1-methylethyl)-benzylamine.

Provenance & Evidence