Benzylamine → HCID 23206741, compound

Participants

Reaction Steps

Pentachloropyridine (80 g, 320 mmol) is treated with benzyl amine (104 mL, 96 mmol), dissolved in dioxane (1 L) and refluxed for 16 hours. The reaction mixture is cooled to ambient temperature and the precipitated white solid is removed by filtration. The filtrate is concentrated to a brown residue and triturated with 4% ethyl acetate in hexane (3×250 mL) to give 4-benzylamino-2,3,5,6-tetrachloropyridine as an off-white solid (40 g, 124 mmol). This material is dissolved in chloroform (400 mL), cooled in an ice bath and treated with trifluoroacetic acid (500 mL) and 30% hydrogen peroxide (100 mL). The reaction mixture is warmed to room temperature overnight and treated with additional trifluoroacetic acid (500 mL) and 30% hydrogen peroxide (100 mL). After stirring 24 hours the reaction is treated with water (1 L). The lower organic layer is separated and the aqueous layer is extracted with chloroform. The combined organic layers are concentrated to a solid residue and redissolved in ethyl acetate/hexane (30 mL). The suspended orange solid is removed and the filtrate is loaded on a silica flash column. The column is eluted with hexane and the title compound is collected as a white solid (15.6 g, 60 mmol). EI MS m/z 260, 262, 264 [M+].

Provenance & Evidence