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

HRID 2211216Notes

Reaction equation

HRID 2211216 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][N:10]1CCCC1=O>>[NH2:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 5770153-Aminopyridine-2-carbonitrile

Procedure

A mixture of 3-Amino-2-chloropyridine (5 g) and cuprous cyanide (5g) in 10 mL of N-Methylpyrrolidone was heated with stirring at 185° C. for 2h under an atmosphere of nitrogen. The reaction mixture was concentrated in vacuo and concentrated ammonium hydroxide and 10% methanol/methylene chloride were added. The mixture was shaken and filtered, the organic layer separated and the aqueous layer extracted two times with methanol/methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvent removed in vacuo. The residue was recrystallized from ethyl acetate/hexane to afford 3-Amino-2-cyanopyridine as a tan solid.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated in vacuo and concentrated ammonium hydroxide and 10% methanol/methylene chloride
  3. additionwere added
  4. filtrationfiltered
  5. customthe organic layer separated
  6. extractionthe aqueous layer extracted two times with methanol/methylene chloride
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. customthe solvent removed in vacuo
  9. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1725127f95ca45f784fbf319efdce412
Source dataset
uspto-grants-1995_10
Patent number
US05463054

Reaction notes

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