Hydrochloric Acid → 4-(1-Aminocyclopropyl)benzonitrile

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.

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

ORD record

ord-404e37ccbb864b1fa84cfbf7fc1ab6b8

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828987B2