2,6-Dichloro-3-nitropyridine → 6-Chloro-3-nitropyridine-2-carbonitrile

HRID 1485511Notes

Reaction equation

HRID 1485511 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[Cu][C:13]#[N:14]>CN1C(=O)CCC1>[Cl:11][C:4]1[N:3]=[C:2]([C:13]#[N:14])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 852392,6-Dichloro-3-nitropyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 133817056-Chloro-3-nitropyridine-2-carbonitrileYield 44.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 2,6-dichloro-3-nitropyridine (6.00 g, 31.1 mmol) in NMP (23.0 mL) was added copper(I) cyanide (3.06 g, 34.2 mmol) at room temperature. After stirred for 40 min at 180° C., the reaction mixture was cooled to room temperature, and then poured into ice water. After stirring for 10 min, the mixture was extracted with EtOAc, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=10:1) to give 6-chloro-3-nitropicolinonitrile (2.54 g, 44%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 7.79 (1H, d, J=8.4 Hz), 8.58 (1H, d, J=8.4 Hz).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. stirringAfter stirring for 10 min
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=10:1)

Sources & evidence

ORD record
ord-4de656b40a284869bf188497b4d790c8
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

Loading…