Hydrochloric Acid → Pyridine, 2,3,5-trichloro-

HRID 1389546Notes

Reaction equation

HRID 1389546 reaction equation
[ClH:1].[Cl:2][CH:3]([CH2:6][C:7]([Cl:11])(Cl)[CH:8]=O)[C:4]#[N:5]>CN(C)C=O>[Cl:1][C:8]1[C:7]([Cl:11])=[CH:6][C:3]([Cl:2])=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 129361852,4,4-Trichloro-5-oxopentanenitrile

Product 1

HCID 27666Pyridine, 2,3,5-trichloro-Yield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydrogen chloride is passed into a solution of 25.0 g (0.125 mol) of 2,4,4-trichloro-4-formylbutyronitrile in 50 mml of N,N-dimethylformamide at a rate such that the temperature of the reaction mixture does not exceed 120° C. After completion of the reaction, the reaction mixture is poured into ice water. The beige-coloured precipitate is filtered off and dried. There is obtained 15.1 g (66% of theory) of 2,3,5-trichloropyridine, m.p. 48°-50° C.

Workup

  1. customdoes not exceed 120° C
  2. customAfter completion of the reaction
  3. filtrationThe beige-coloured precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-ad586ac676814a4fb26d43aafef2631c
Source dataset
uspto-grants-1981_01
Patent number
US04245098

Reaction notes

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