Ammonium Chloride → 2,5,6-Trichloropyridine-3-carbonitrile

HRID 75944Notes

Reaction equation

HRID 75944 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[C:6](Cl)[C:3]=1[C:4]#[N:5].[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 7286742,4,5,6-Tetrachloronicotinonitrile

Product 1

HCID 229063392,5,6-Trichloropyridine-3-carbonitrileYield 71.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2,4,5,6-tetrachloronicotinonitrile (7.6 g, 31.4 mmol) in MeOH/THF (230 ml/230 ml) was added zinc dust (4.0 g, 62.8 mmol) slowly at 0° C. and the saturated NH4Cl solution (105 ml) and the mixture was stirred for 30 minutes. TLC indicated that the reaction is complete. Saturated NH4OAc solution (180 ml) was added to the mixture and the mixture was allowed to stir at room temperature for 30 minutes. The mixture was filtered and was washed with EtOAc (500 ml). The filtrate was washed with brine and dried and concentrated to give a solid. ISCO column purification gave the title compound (4.63 g, 71%). 1H NMR (CDCl3): δ 8.97 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. washwas washed with EtOAc (500 ml)
  3. washThe filtrate was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a solid
  7. customISCO column purification

Sources & evidence

ORD record
ord-c37fb263623b4be2838022fe009a53b2
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

Loading…