Chloride → 4-(2-Chloroethyl)pyridine hydrochloride

HRID 615586Notes

Reaction equation

HRID 615586 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

5

Reactant 3

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 729214-Pyridineethanol

Product 1

HCID 124817414-(2-Chloroethyl)pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Sources & evidence

ORD record
ord-d3ad9075caa14c78a5d60ff7e1306ae2
Source dataset
uspto-grants-1985_02
Patent number
US04500535

Reaction notes

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