Diethyl Ether → 6-Chloro-4-methylpyridine-2-carbonitrile

2-chloro-4-methylpyridine 1-oxide (8.5 g, 59.2 mmol) from step 1 of this example was added to the dimethyl sulfate (9.0 g, 71 mmol) and the mixture stirred overnight. Diethyl ether (40 ml) was added, the mixture stirred, and ether decanted (2×). The volatiles were removed in vacuum. The residue was dissolved in water (50 ml) and the solution added drop wise to a −15° C. solution of sodium cyanide (11.3 g, 231 mmol) in water (50 ml) under N2. The mixture was stirred between −7 and −15° C. for 1.5 hours during which a solid precipitates. The crystals were filtered, washed with water followed by a small amount of cold ether to give the titled compound. LRMS calc: 152.01; obs: 153.56 (M+1).

1. stirringthe mixture stirred
2. customether decanted (2×)
3. customThe volatiles were removed in vacuum
4. dissolutionThe residue was dissolved in water (50 ml)
5. stirringThe mixture was stirred between −7 and −15° C. for 1.5 hours during which a solid
6. customprecipitates
7. filtrationThe crystals were filtered
8. washwashed with water

ORD-Eintrag

ord-dd28de97a9e443e19bf9cfa60d2caea2

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08552022B2