Hydrochloric Acid → 4-(1-Aminocyclopropyl)benzonitrile

HRID 72396

반응식

HRID 72396 반응식
[C:1](#[N:10])[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:11]([Mg]Br)[CH3:12].B(F)(F)F.CCOCC.Cl>ClCCl.C(OCC)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[NH2:7][C:6]1([C:5]2[CH:8]=[CH:9][C:2]([C:1]#[N:10])=[CH:3][CH:4]=2)[CH2:12][CH2:11]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 121721,4-DicyanobenzeneHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 451402064-(1-Aminocyclopropyl)benzonitrile

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of terephthalonitrile (3.30 g, 25.8 mmol.) in dichloromethane (130 ml), Titanium (IV) isopropoxide (7.6 ml, 25.8 mmol) was added at room temperature followed by dropwise addition of ethyl magnesium bromide 1M in diethyl ether (47.0 ml). The mixture was stirred at room temperature for 45 min, then boron trifluoride etherate (5 ml) was added at once. After 2 hours, HCl aqueous solution (5%) was added to quench the reaction. The aqueous phase was separated, basified with aqueous 1M NaOH and extracted with ethylacetate. The organic phase was dried over Na2SO4 and concentrated under vacuo. The residue was purified by column chromatography eluting with a mixture petroleum ether/ethyl acetate (5:1). Collected fractions after solvent evaporation afforded the title compound (D14) (500 mg) as a white solid.

후처리

  1. waitAfter 2 hours
  2. customto quench
  3. customthe reaction
  4. customThe aqueous phase was separated
  5. extractionextracted with ethylacetate
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated under vacuo
  8. customThe residue was purified by column chromatography
  9. washeluting with a mixture petroleum ether/ethyl acetate (5:1)
  10. customCollected fractions after solvent evaporation

출처 및 근거

ORD 기록
ord-404e37ccbb864b1fa84cfbf7fc1ab6b8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828987B2

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