Hydroxyacetone → 1-Propanol, 2-[(2,3,4-trifluorophenyl)amino]-

Participants

Reaction Steps

2,3,4-trifluoroaniline was reductively alkylated in the presence hydroxyacetone using a Raney Nickel catalyst. Raney nickel (14 ml of 50% aqueous Raney nickel catalyst was slurried in 100 ml of absolute methanol. The mixture was allowed to settle and 90-95% of the liquid was decanted. The process was then repeated three times. 2,3,4-Trifluoroaniline (7.3 g, 0.05 mole) was charged into a glass autoclave liner containing the catalyst. Hydroxyacetone (3.7 g, 0.05 mole) was then added and the mixture was purged with nitrogen. Hydrogenation was initiated at 65° C. and continued to a maximum temperature of 85° C. Hydrogen uptake continued for 0.5 hour between 430 and 450 psi at which time 75% of the alkylated product (3) was obtained with the remainder being unreacted 2,3,4-trifluoroaniline and hydroxyacetone.

Provenance & Evidence