Hydrazine → HCID 14698017, compound

Participants

Reaction Steps

To a vial were added 5-(2-nitrophenyl)-1H-imidazole (200 mg, 1.06 mmol), ferric chloride (8.6 mg, 0.35 mmol), activated carbon (2.2 mg, 1.80 mmol) and hydrazine (1.1 ml, 21.2 mmol) and methanol (9 mL). The resulting mixture was stirred at r.t. for 5 min then was heated to 70° C. for two days. The reaction was cooled to room temperature and filtered. The filtrate was concentrated and purified to give 2-(1H-imidazol-5-yl)aniline. The intermediate was dissolved in acetic acid (2 ml) and formaldehyde (37% in water, 0.3 ml) was added. The reaction was stirred for 1 h at room temperature, diluted with 30 ml ethyl acetate, and extracted with 5% HCl. The aqueous layer was basified with K2CO3 (add gradually until PH=7), then extracted with ethyl acetate (30 mL*2). The organic layer was evaporated under reduced pressure and product was obtained by column chromatography using ethyl acetate as eluent (26% yield). 1H NMR: 4.70 (s, 1H), 4.93 (s, 2H), 7.50-7.56 (m, 1H), 7.73-7.82 (m, 3H), 8.24-8.31 (m, 2H).

Provenance & Evidence