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

HRID 249077

반응식

HRID 249077 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 5770153-Aminopyridine-2-carbonitrile

반응 조건

온도
185 °C

실험 절차

A mixture of 3-Amino-2-chloro-pyridine (5 g) 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

후처리

  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

출처 및 근거

ORD 기록
ord-fbffb0a1d8894513b8ee9de8211916be
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212310

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