Ethanol → HCID 86725498, compound

Temperature

80 °C

To a stirred solution of 2-(5-phenyl-1H-pyrazol-1-yl)isonicotinonitrile (100 mg, 0.41 mmol) in EtOH (10 mL) was added a solution of 25% NaOH in water (1.0 mL). The reaction mixture was heated under reflux conditions at 80° C. for 1 h. After reaction completion, the solvent was removed, and the resultant mixture was diluted with water, and the pH was adjusted to pH=4-5 with 2.0 N HCl. The mixture was extracted with EtOAc (3×15 mL), the combined organic layers were dried over Na2SO4, and the solvent was removed to obtain pale yellow solid, which was washed with hexane and dried under reduced pressure to afford the title compound (60 mg, 55% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.5(S, 1H), 8.2 (d, 1H, J=2.1 Hz), 7.9 (s, 1H), 7.78 (s, 1H), 7.7 (d, 1H, J=2.7 Hz), 7.3 (m, 2H), 7.2 (m, 1H), 6.65 (s, 2H). [M+H] Calc'd for C15H11N3O2, 266; Found, 266.

1. customAfter reaction completion
2. customthe solvent was removed
3. additionthe resultant mixture was diluted with water
4. extractionThe mixture was extracted with EtOAc (3×15 mL)
5. dry with materialthe combined organic layers were dried over Na2SO4
6. customthe solvent was removed
7. customto obtain pale yellow solid, which
8. washwas washed with hexane
9. customdried under reduced pressure

ORD record

ord-0aeed9b8cac7460dafccd6e29931ea34

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987461B2