Ammonium Chloride → 2,5,6-Trichloronicotinonitrile

HRID 2189904Notes

Reaction equation

HRID 2189904 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-TrichloronicotinonitrileYield 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-07959ee71e8a4dfbaada211d8fbb3fa4
Source dataset
uspto-grants-2012_12
Patent number
US08324252B2

Reaction notes

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