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

Temperature

185 °C

A mixture of 3-Amino-2-chloro-pyridine (5g) and cuprous cyanide (5 g) in 10 mL of N-Methylpyrrolidone was heated with stirring at 185° C. for 2 h 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.

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

ORD record

ord-6c7d776b79164a5b9321eb6af0803ddc

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05625063