Phenol → HCID 66814468, compound

Participants

Reaction Steps

Sodium hydride (19.8 g of a 60% dispersion in mineral oil, 0.495 mol) in tetrahydrofuran (THF) (450 mL) was cooled to 0° C.; a solution of phenol (77.7 g, 0.826 mol) in THF (150 mL) was added slowly over a period of 30 minutes. The reaction was stirred at ambient temperature for 30 minutes, and a solution of 2-chloro-5,6-dimethyl-4-(2-methylpropyl)-3-nitropyridine (60.78 g, 0.236 mol) in THF (350 mL) was added. The reaction was heated to 70° C., heated at 50° C. overnight, allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (800 mL). The resulting solution was washed sequentially with 1 N aqueous sodium hydroxide (1×800 mL), brine (3×400 mL), 1 N aqueous sodium hydroxide (1×400 mL), brine (1×400 mL), 1 N aqueous sodium hydroxide (1×400 mL), and deionized water (1×400 mL); dried over magnesium sulfate; filtered through a layer of CELITE filter agent; concentrated under reduced pressure; and further dried overnight under high vacuum to provide 80.46 g of 5,6-dimethyl-N-(2-methylpropyl)-3-nitro-2-phenoxypyridin-4-amine as an orange-red solid containing some mineral oil.

Provenance & Evidence