Trimethylamine → 3-Amino-5-methylbenzotrifluoride

Participants

Reaction Steps

At room temperature, 32.3 gms of crude nitrated product from Example V was added to a mixture of 150 ml MeOH and 30 gms (2.5 eq) of trimethylamine. The dark solution was charged with 1.6 gms of 50% wet 5% Pd/C catalyst and hydrogenated for 48 hours at 60° C. with hydrogen at 4 atms. The final solution was concentrated by distilling about half of the MeOH, diluted with 250 ml H2O and washed 3 times with 100 ml CH2Cl2. All of the organic extractions were combined, dried (Na2SO4), filtered and concentrated to 24 gms of a dark liquid which was Kugelrohr distilled at 95°-110° C./32 mm to 17.6 gms of light yellow colored crystals of 3-methyl-5-amino benzotrifluoride; mp 27°-28° C. (83% yield).

Provenance & Evidence