Hydroxyamine hydrochloride → 3-(Cyclopentyloxy)-4-methoxybenzonitrile
Reaction equation
Cl.[NH2:2]O.[CH:4]1([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[CH:13]=O)[CH2:8][CH2:7][CH2:6][CH2:5]1>C(OC(=O)C)(=O)C>[CH:4]1([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[C:13]#[N:2])[CH2:8][CH2:7][CH2:6][CH2:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
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%.].