Aluminum(III) Chloride → 2,3,5-Trichloropyridine

Reaction equation

[Cl:1][CH:2]([CH2:5][C:6]([Cl:10])(Cl)[CH:7]=O)[C:3]#[N:4].[Al+3].[Cl-:12].[Cl-].[Cl-]>>[Cl:12][C:7]1[C:6]([Cl:10])=[CH:5][C:2]([Cl:1])=[CH:3][N:4]=1

Participants

Reactant 2

HCID 6451240Aluminum(III) Chloride

HCID 129361852,4,4-Trichloro-5-oxopentanenitrile

Product 1

HCID 276662,3,5-Trichloropyridine

Conditions

Temperature: 60 °C

Procedure

13.6 g of 2,4,4-trichloro-4-formylbutyronitrile obtained according to (a), with the addition of 1.0 g of AlCl3, is heated in an enamel autoclave for 1 hour at 60° C. The dark crude product is afterwards distilled with steam, in the process of which the 2,3,5-trichloropyridine precipitates, in the distillate, in the form of white crystals. The yield is 9.1 g (83% of theory) of 2,3,5-trichloropyridine, m.p. 49°-50° C.

Workup

distillationThe dark crude product is afterwards distilled with steam, in the process of which the 2,3,5-trichloropyridine
customprecipitates, in the distillate, in the form of white crystals

Sources & evidence

ORD record: ord-5cb2fca8d0924c639ac1e07b499be8b3
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04245098

Reaction notes

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