Ammonium Hydroxide → HCID 59191360, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-ethyl-2-methoxyphenoxy)-3-fluoroaniline (215 mg; 0.82 mmol) in H2SO4 35%, at 0° C., was added a solution of NaNO2 (69 mg; 1 mmol) in water (1 mL). The mixture was stirred 30 min. at 0° C. A solution of copper(II) sulphate (1.85 g; 11.6 mmol) in 6 mL of water was added, followed by copper(I) oxide (99 mg; 0.69 mmol). The reaction was stirred 45 min. at room temperature, then hydrolysed with NaHCO3 sat (6 mL) and NH4OH. The mixture was extracted with ethyl acetate (3*5 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (85 mg; 0.032 mmol; 39%) was obtained as an oil, after purification by preparative TLC (cyclohexane/ethyl acetate: 7/3).

Provenance & Evidence