Sodium Hydroxide → HCID 19878937, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-2',4,4',5,5'-pentachlorobiphenyl was prepared from 2-Nitro-2',4,4',5,5'-pentachlorobiphenyl (2.5 g, 6.8 mmol) by dissolving the compound in acetic acid (60 mL) heated to 100° C. and adding a solution of SnCl2 (6 g) in concentrated HCl (30 mL). The temperature was raised to reflux for 3 h, then the reaction mixture was allowed to cool to ambient temperature, whereupon it was poured into ice (100 g). The pH of the solution was adjusted to 9 with NaOH and then extracted with methylene chloride (2×100 mL). The extract was washed with NaOH (1N, 2×25 mL) and water (100 mL); dried over MgSO4 and filtered to give the impure amine. The crude product was chromatographed in two equal batches (Chromatotron®, Harrison Research, Palo Alto, Calif., 4 mm silica gel, step gradient from hexanes to 10% ethyl acetate in hexanes, 20 mL/min) to give the title hapten (830 mg). Mass spectrum: m/z at 340 (M+1) for C12H6Cl5N.

Provenance & Evidence