Hydrochloric Acid → HCID 53401469, compound

Temperature

50 °C

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.

1. customThe flask was fitted with a reflux condenser
2. temperatureThe mixture was then cooled to room temperature
3. stirringThe reaction was stirred until the bubbling
4. concentrationThe mixture was then concentrated in vacuo
5. extractionthe residue was extracted with CHCl3/MeOH/water (8:1:1) (×2)
6. dry with materialThe combined extracts were dried over Na2SO4
7. filtrationThe inorganics were filtered off
8. customthe solvent was removed in vacuo

ORD record

ord-a406469bbf63440abbaf1c1cad4b4efc

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2