Hydrochloric Acid → HCID 53401469, compound

Participants

Reaction Conditions

Reaction Steps

5-(trifluoromethyl)nicotinonitrile (0.31 g, 1.95 mmol, 1 eq) and CoCl2.6H2O (0.23 g, 0.97 mmol, 0.5 eq) were dissolved in 10 mL EtOH. The flask was fitted with a reflux condenser and heated to 50° C. under Ar. NaBH4 (0.22 g, 5.85 mmol, 3 eq) was added in 2 batches and the mixture was stirred at 50° C. for 2 h. The mixture was then cooled to room temperature and 5 N HCl was added to pH=1-2. The reaction was stirred until the bubbling stopped and NH4OH (28%) was added to pH=9. The mixture was then concentrated in vacuo and the residue was extracted with CHCl3/MeOH/water (8:1:1) (×2). The combined extracts were dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo yielding 0.1 g (0.61 mmol, 31% yield) of (5-(trifluoromethyl)pyridin-3-yl)methanamine.

Provenance & Evidence