Hydrochloric Acid → α-(Dimethylamino)-2-pyridineacetonitrile

HRID 1605679Notes

Reaction equation

HRID 1605679 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH3:9][NH:10][CH3:11].Cl.[C-:13]#[N:14].[K+]>O>[CH3:9][N:10]([CH3:11])[CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:13]#[N:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 9032Potassium CyanideHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 15166870α-(Dimethylamino)-2-pyridineacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To cold 2-pyridinecarboxaldehyde (21.4 g., 0.2 mole) is added dimethylamine (22.5 g. of a 40% aqueous solution, 0.2 mole) and the solution is neutralized with concentrated hydrochloric acid. To the stirred neutralized solution is added 14.4 g. (0.22 mole) of potassium cyanide. The mixture is stirred overnight, then diluted with water, transferred to a separatory funnel and repeatedly extracted with chloroform. The combined chloroform extracts are washed 3 times with water, once with brine and dried over magnesium sulfate. The mixture is filtered, the solvent is removed under reduced pressure and methanol is added to the residue. The mixture is allowed to stand at -20°C. for 18 hours, then filtered. The filtrate is concentrated and distilled in vacuo to give 2-dimethylamino-2-(2-pyridyl)acetonitrile.

Workup

  1. additionTo the stirred neutralized solution is added 14.4 g
  2. customtransferred to a separatory funnel
  3. extractionrepeatedly extracted with chloroform
  4. washThe combined chloroform extracts are washed 3 times with water
  5. dry with materialonce with brine and dried over magnesium sulfate
  6. filtrationThe mixture is filtered
  7. customthe solvent is removed under reduced pressure and methanol
  8. additionis added to the residue
  9. waitto stand at -20°C. for 18 hours
  10. filtrationfiltered
  11. concentrationThe filtrate is concentrated
  12. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-bef9b3d7c7114b29bc3b0cbf45a3e035
Source dataset
uspto-grants-1976_04
Patent number
US03950522

Reaction notes

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