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

HRID 2359437Notes

Reaction equation

HRID 2359437 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.[C:12]([Cu])#[N:13]>CN1CCCC1=O>[Cl:11][C:4]1[N:3]=[C:2]([C:12]#[N:13])[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 41.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2,6-dichloro-3-nitropyridine (40 g, 207 mmol) and CuCN (22.32 g, 248 mmol) in 1-methyl-2-pyrrolidinone (160 ml) was quickly heated to 180° C. for 25 minutes. The mixture was cooled to room temperature and the deep brown solution was poured into ice water (1200 ml) and stirred for 30 min. The aqueous solution was extracted with ethyl acetate and boiling toluene, the organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (5% to 25% Ethyl Acetate gradient in Pentane) to give 6-chloro-3-nitropicolinonitrile as a yellow solid. (15.75 g, 41.4% yield)

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography (5% to 25% Ethyl Acetate gradient in Pentane)

Sources & evidence

ORD record
ord-872f3591db484d73ae99df93f646bc6a
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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