Hydrazine → HCID 14698017, compound

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).

1. temperaturethen was heated to 70° C. for two days
2. temperatureThe reaction was cooled to room temperature
3. filtrationfiltered
4. concentrationThe filtrate was concentrated
5. custompurified

ORD record

ord-e5941c7715084b7ab513f2efb40c6fbf

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722720B2