Hydrochloric Acid → 6-Chloro-3-pyridinecarbonitrile

HRID 2210668Notes

Reaction equation

HRID 2210668 reaction equation
C(O[CH:4]=[C:5]([C:10]#[N:11])[CH:6]=[CH:7][C:8]#[N:9])C.[ClH:12]>C(O)(=O)C>[Cl:12][C:8]1[CH:7]=[CH:6][C:5]([C:10]#[N:11])=[CH:4][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53803557HCID 53803557, compound

Product 1

HCID 51520946-Chloro-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 30 g of ethoxymethylene-glutacononitrile in 300 ml of glacial acetic acid was cooled to 0° C. and saturated with HCl gas. The mixture was allowed to rise to room temperature and left to stand overnight. It was concentrated and the residue was stirred together with 70 ml of water and neutralized with NaHCO3 solution. After being filtered off and recrystallized from ethanol, 2-chloro-5-cyanopyridine was obtained in 73.5% of the theoretical yield.

Workup

  1. customto rise to room temperature
  2. waitleft
  3. concentrationIt was concentrated
  4. filtrationAfter being filtered off
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ecf3fba2f70e446787f54b5e35731df5
Source dataset
uspto-grants-1995_10
Patent number
US05459273

Reaction notes

Loading…