N-methyl-2-pyrrolidone → 3-Chloropyridine-2-carbonitrile

HRID 713652Notes

Reaction equation

HRID 713652 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]1C(=O)CCC1>[C-]#N.[Zn+2].[C-]#N.O>[Cl:8][C:7]1[C:2]([C:9]#[N:10])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 169882,3-Dichloropyridine

Product 1

HCID 8182583-Chloropyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 29.6 g of 2,3-dichloropyridine, 46.97 g of zinc cyanide, 11.56 g of tetratris(triphenylphosphine)palladium(0) and 150 mL of NMP was stirred at 100° C. for 2 hours. Water was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 9.08 g of 3-chloropyridine-2-carbonitrile.

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c7ece08dbc64efd844aa30e1ed29f53
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

Loading…