5-(Chloromethyl)picolinonitrile hydrochloride synthesis

2synthesis methods

Product Name:5-(Chloromethyl)picolinonitrile hydrochloride
CAS Number:1225380-31-3
Molecular formula:C7H6Cl2N2
Molecular Weight:189.0419

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5-(Chloromethyl)picolinonitrile hydrochloride

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Yield: 75%

Reaction Conditions:

with thionyl chloride in dichloromethane at 0 - 20; for 6 h;

Steps:

40A
272 μl (3.73 mmol) of thionyl chloride were added to a solution of 250 mg (1.86 mmol) of 5-(hydroxymethyl)pyridine-2-carbonitrile [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 5 ml of anhydrous methylene chloride at 0° C. The reaction mixture was then stirred at RT for 6 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained was dried under a high vacuum. 263 mg (75% of th.) of the title compound were obtained.¹H-NMR (400 MHz, CDCl₃, δ/ppm): 8.73 (d, 1H), 7.90 (dd, 1H), 7.72 (d, 1H), 4.63 (s, 2H).MS (ESIpos): m/z=153/155 (³⁵Cl/³⁷Cl) [M+H]⁺.LC/MS (method F, ESIpos): R_t=0.75 min, m/z=153/155 (³⁵Cl/³⁷Cl) [M+H]⁺.

References:

BAYER SCHERING PHARMA AKTIENGESELLSCHAFT US2011/301122, 2011, A1 Location in patent:Page/Page column 42

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2-Pyridinecarbonitrile, 5-[[(methylsulfonyl)oxy]methyl]-

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References