Hydroxyamine hydrochloride → 3-(Cyclopentyloxy)-4-methoxybenzonitrile

Temperature

100 °C

Hydroxylamine hydrochloride (3.82 g) is added to a solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (11.0 g) in acetic anhydride (30 mL) and the suspension heated in an oil bath at 100° C. until refluxing starts. The heating is then removed while the exothermic reaction refluxes gently. Heating at 100° C. is then continued for a further 1 hour. The dark solution is concentrated and the crude product dissolved in cyclohexane (200 mL). The solution is washed with 5% sodium bicarbonate solution (2×50 mL), water (2×50 mL) and brine (50 mL), and dried over magnesium sulfate. Upon evaporation, an amber oil (11.8 g) that is purified by flash chromatography (dichloromethane as eluant on silica column) gives 3-cyclopentyloxy-4-methoxybenzonitrile (8.6 g) as a pale yellow oil. [Elemental analysis: C,71.7; H,6.93; N,6.47%; calculated for C13H15NO2 : C,71.87; H,6.96; N,6.45%.].

1. temperatureuntil refluxing starts
2. customThe heating is then removed while the exothermic reaction
3. temperatureHeating at 100° C.
4. concentrationThe dark solution is concentrated
5. dissolutionthe crude product dissolved in cyclohexane (200 mL)
6. washThe solution is washed with 5% sodium bicarbonate solution (2×50 mL), water (2×50 mL) and brine (50 mL)
7. dry with materialdried over magnesium sulfate
8. customUpon evaporation
9. customan amber oil (11.8 g) that is purified by flash chromatography (dichloromethane as eluant on silica column)

ORD record

ord-5a22f9414e4644d79b5bd6e17daf36b1

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05840724