3-Methoxyphenylhydrazine hydrochloride → (3-Methoxyphenyl)hydrazine

Participants

Reaction Steps

3-Methoxyphenylhydrazine hydrochloride (1 g) was suspended in 1 M aqueous NaOH solution and extracted with ether. The organic phase was dried (MgSO4), filtered and concentrated to dryness to give 3-methoxyphenylhydrazine. 2,5-Dibromobenzaldehyde (1 g) and N-methylpyrrolidone (3.7 ml) were added and the mixture was heated under microwave conditions to 160° C. for 10 min. K2CO3 (1.015 g), Cul (36 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (53 mg) were added and the mixture was heated under microwave conditions to 160° C. for 40 min. Cul (18 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (26 mg) were added and the mixture was heated under microwave conditions to 160° C. for 20 min. The mixture was filtered and the filtrate was concentrated. The product was purified by chromatography (SiO2, CH2Cl2/MeOH 100:0=>95:5) to give the title compound (659 mg) as a yellow oil. MS (m/e)=303.0 [M+H+].

Provenance & Evidence