Water → 6-(3-Hydroxypropoxy)nicotinonitrile

Sodium hydride (0.42 g, 60% suspension in mineral oil, 10.61 mmol) was added to a solution of 1,3-propanediol (2.30 mL, 31.83 mmol) in DMF (22 mL) at 0° C., and the mixture was stirred at rt for 20 minutes. To the resultant pale yellow slurry was added 6-chloronicotinonitrile (1.50 g, 10.61 mmol) in one portion. The mixture was stirred at rt for 18 h. It was then poured into water. The precipitates were filtered and the filtrate was extracted with ethyl acetate. The organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (1.56 g, 83%) as a white solid. 1H NMR (300 MHz, CD2Cl2) δ 8.47 (d, 1H), 7.82-7.79 (m, 1H), 6.84-6.82 (m, 1H), 4.53 (t, 2H), 3.75 (t, 2H), 2.06-1.99 (m, 2H).

1. stirringThe mixture was stirred at rt for 18 h
2. filtrationThe precipitates were filtered
3. extractionthe filtrate was extracted with ethyl acetate
4. extractionThe organic extract
5. washwas washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-7fc2969898564c098ca82b381c016147

Quelldatensatz

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07592361B2