Hydrochloric Acid → 2,3,5-Trichloropyridine

Reaction equation

[Cl:1][CH:2]([CH2:5][C:6]([Cl:10])(Cl)[CH:7]=O)[C:3]#[N:4].[ClH:11]>>[Cl:11][C:7]1[C:6]([Cl:10])=[CH:5][C:2]([Cl:1])=[CH:3][N:4]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 129361852,4,4-Trichloro-5-oxopentanenitrile2×

Product 1

HCID 276662,3,5-Trichloropyridine

Procedure

The 2,4,4-trichloro-4-formyl-butyronitrile (17.3 g) obtained according to (a) is heated, as a weak stream of hydrogen chloride is being introduced, at 80°-85° C. for 24 hours. The entire reaction mixture is subsequently distilled with steam. The yield is 10.0 g (72% of theory) of 2,3,5-trichloropyridine in the form of white crystals, m.p. 49°-50° C.

Workup

additionis being introduced, at 80°-85° C. for 24 hours
customThe entire reaction mixture
distillationis subsequently distilled with steam

Sources & evidence

ORD record: ord-508772a2e1d84a919886ccbd52e62fa2
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04245098

Reaction notes

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