Ethyl Acetate → 2-(6-Chloropyridazin-3-yl)acetonitrile

Temperatur

80 °C

3-Chloro-6-chloromethyl-pyridazine (1.50 g) dissolved in dimethyl sulfoxide (7.5 mL) was added to a solution of potassium cyanide (0.90 g) in water (1 mL) and dimethyl sulfoxide (7.5 mL) stirred at 80° C. The solution was stirred at this temperature for 30 min and then cooled to room temperature. Water and ethyl acetate were added and the resulting mixture was filtered over Celite. The aqueous phase of the filtrate was separated and extracted twice with ethyl acetate. The extracts and the organic phase of the filtrate were combined and washed with brine and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1) to give the title compound as a solid. Yield: 0.23 g (16% of theory); LC (method 2): tR=0.76 min; Mass spectrum (ESI+): m/z=154/156 (Cl) [M+H]+.

1. stirringThe solution was stirred at this temperature for 30 min
2. temperaturecooled to room temperature
3. filtrationthe resulting mixture was filtered over Celite
4. customThe aqueous phase of the filtrate was separated
5. extractionextracted twice with ethyl acetate
6. washwashed with brine
7. dry with materialdried (Na2SO4)
8. customThe solvent was evaporated
9. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1)

ORD-Eintrag

ord-708ad7f3926d4a229455214a5e5eacbc

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08933072B2