Water → 5-Hydroxypyridine-3-carbonitrile

Temperature

0 °C

5-Hydroxynicotinamide (0.69 g, 5 mmol) prepared by the method described in International Patent Publication No. 8606628 was dissolved in pyridine (50 ml). Trifluoroacetic anhydride (2.52 g, 12 mmol) was added, and the mixture was stirred at 0° C. for 20 hours. The reaction mixture, to which water (20 ml) was added, was concentrated under reduced pressure and extracted with chloroform (50 ml×3). The chloroform layer was washed with water (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (Wako Gel C-200, 20 g; eluted with chloroform:methanol=100:1) to give 3-cyano-5-hydroxypyridine (0.42 g, 3.5 mmol) (Yield 70%).

1. concentrationwas concentrated under reduced pressure
2. extractionextracted with chloroform (50 ml×3)
3. washThe chloroform layer was washed with water (50 ml)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customto give a residue
7. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 20 g; eluted with chloroform:methanol=100:1)

ORD record

ord-b3969444477b436c82510515b1255be8

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05508293