HCID 15091343, compound → 80653-80-1

Participants

Reaction Steps

B-2. 2-Nitro-5-(4-pyridinyl)phenol--This compound along with two other isomers, namely, 4-nitro-3-(4-pyridinyl)phenol and 2-nitro-3-(4-pyridinyl)phenol (Example B-3), were all obtained when 3-(4-pyridinyl)phenol was nitrated as in Example B-1. To an ice cold mixture of 242 g. of 3-(4-pyridinyl)phenol and 1 liter of glacial acetic acid was added with stirring a solution containing 60 ml. of concentrated nitric acid in 200 ml. of glacial acetic acid over a 40 minutes period, maintaining the reaction temperature between 10°-15° C. The reaction mixture was stirred at room temperature for 1 hour, next gently heated on a steam bath for 4 hours and then allowed to stand at ambient temperature for 16 hours. The reaction mixture was concentrated on a rotary evaporator to remove about 700 ml. of acetic acid. The resulting slurry was poured into 1 liter of water and was neutralized by adding aqueous ammonium hydroxide. The resulting solid was collected, washed with water and dried at 80° C. It was crystallized from acetic acid (2 l.), collected and dried at 80° C. to produce 50.4 g. of 4-nitro-3-(4-pyridinyl)phenol, m.p.>300° C. The mother liquor was concentrated to give another 34 g. of crude 4-nitro-3-(4-pyridinyl)phenol.

Provenance & Evidence