Water → 1-(5-Chloropyridin-3-yl)methanamine

A mixture of 5-chloro-nicotinonitrile (63.8 mg, 461 μmol), 2-propanol (9.2 mL; not dry), and CaSO4 (−325 mesh) (920 mg, 6.76 mmol) was treated with a suspension of Raney Cobalt 2700 in 2-propanol under air (2 mL) (prepared by diluting 2 mL of the commercial water slurry with 15 mL 2-propanol, centrifuging, decanting, and repeating with 2×15 mL 2-propanol, then resuspending with 2 mL 2-propanol). The flask was then sealed and evacuated until bubbles formed, and the evacuated flask was flushed with H2 gas via balloon pressure. After 11 h stirring at rt under balloon H2 pressure, a NMR spectrum of a worked-up reaction aliquot indicated 80% conversion to the title compound. The reaction was then filtered, the filter cake was washed with 2-propanol (3×10 mL), and the combined clear colorless filtrates were concentrated briefly under rotary evaporation at 50° C. The residue was taken up in DCM and concentrated again to afford the volatile crude title compound (53 mg, 81%).

1. customprepared
2. customdecanting
3. customThe flask was then sealed
4. customevacuated until bubbles
5. customformed
6. customthe evacuated flask was flushed with H2 gas via balloon pressure
7. customa NMR spectrum of a worked-up reaction aliquot indicated 80% conversion to the title compound
8. filtrationThe reaction was then filtered
9. washthe filter cake was washed with 2-propanol (3×10 mL)
10. concentrationthe combined clear colorless filtrates were concentrated briefly under rotary evaporation at 50° C
11. concentrationconcentrated again

ORD record

ord-a545cc41a3474cf0a0980b5696ff1fc0

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829584B2