5-Bromonicotinamide → 5-Bromonicotinonitrile

Temperature

25 °C

5-Bromo-3-pyridinylcarboxamide (10 g, 49.7 mmol) in phosphorus oxychloride (25 mL) was warmed to reflux for 18 h, allowed to cool to 25° C., concentrated in vacuo and carefully treated with satd. aqueous sodium bicarbonate (˜500 mL) until neutralized. The reaction mixture was diluted with CH2Cl2 (200 mL), stirred for 4 h, and the layers were separated. The aqueous layer was washed with CH2Cl2 (2×100 mL), and the organic layers were combined and dried (MgSO4). The resulting solution was concentrated in vacuo to afford the title compound (6.35 g, 70%) as a white solid. MS 184 (M+H)+.

1. temperatureto reflux for 18 h
2. concentrationconcentrated in vacuo
3. additioncarefully treated with satd
4. additionThe reaction mixture was diluted with CH2Cl2 (200 mL)
5. customthe layers were separated
6. washThe aqueous layer was washed with CH2Cl2 (2×100 mL)
7. dry with materialdried (MgSO4)
8. concentrationThe resulting solution was concentrated in vacuo

ORD record

ord-30c79bf012b64918808d4c344a0bd047

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06713455B2