Chloride → 4-(2-Chloroethyl)pyridine hydrochloride

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8]O)=[CH:3][CH:2]=1.[Cl-:10].S(Cl)([Cl:13])=O>C(Cl)Cl>[ClH:13].[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][Cl:10])=[CH:3][CH:2]=1

Participants

Procedure

Furthermore 4-picolyl chloride hydrochloride or 4-picolyl bromide hydrobromide is converted to the free base by rendering the salt basic in ethanol, and then reacting with sodium or potassium cyanide (1.05 equivalents) to form the corresponding nitrile. The nitrile is solvolized in ethanol with aqueous hydrochloride acid to form ethyl 4-picolylacetate [cf. Rising et al., J. Am. Chem. Soc. 50, 1211 (1928)]. The latter is reduced with Red-al in benzene-tetrahydrofuran and isolated by the method of Examples 9 and 10, yielding 2-(4-pyridyl)ethanol. The alcohol is converted to corresponding chloride by reaction with thionyl chloride in refluxing methylene chloride [cf. Gilman et al., Rec. trav. chim. 51, 93 (1932)]. The 2-(4-pyridyl)ethyl chloride hydrochloride which forms is isolated by evaporation.