2-Chloroacrylonitrile → 5-Methylpicolinonitrile

HRID 1650338Notes

Reaction equation

HRID 1650338 reaction equation
ClC(=C)C#[N:4].[N:6]1([CH:14]2[CH2:21]CC[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:13]CCCCCN1>C(#N)C>[C:21]([C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[CH:13][N:6]=1)#[N:4]

Participants

4

Reactant 2

HCID 701982-ChloroacrylonitrileHCID 66583054Diazabicyclooctane

Product 1

HCID 741835-Methylpicolinonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

19.6 g of 1-dimethyl-1-aza-3-methyl-1,3-butadiene, 17.5 g of 2-chloroacrylonitrile and 33.6 g of diazabicyclooctane (DABCO) are heated in 200 ml of acetonitrile for 30 hours to reflux. The reaction mixture is concentrated by evaporation and the residue is slightly acidified with 1N HCl and extracted with chloroform. The organic extract is dried and concentrated by evaporation and the residue is distilled. b.p. (6·10-3 bar) 63°-69° C. The distillate is digested with petroleum ether. The title compound is isolated in the form of crystals with a melting point of 72°-74° C.

Workup

  1. temperatureto reflux
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. extractionextracted with chloroform
  4. extractionThe organic extract
  5. customis dried
  6. concentrationconcentrated by evaporation
  7. distillationthe residue is distilled
  8. custom(6·10-3 bar) 63°-69° C

Sources & evidence

ORD record
ord-c62cdb46ee524fc8a3457511d2800e30
Source dataset
uspto-grants-1990_05
Patent number
US04923993

Reaction notes

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