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

HRID 1182931Notes

Reaction equation

HRID 1182931 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-cdc65c1ea7be4624a4590ee59ca6b233
Source dataset
uspto-grants-2014_03
Patent number
US08664230B2

Reaction notes

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