Sulfuric Acid → HCID 12183373, compound

Participants

Reaction Steps

6-chloro-3-(2-methoxyphenyl)pyridin-2-amine (4.0 g, 17.04 mmol) was dissolved in glacial acetic acid (100 mL) and concentrated sulfuric acid (1 mL). A solution of t-butylnitrite (6.1 mL, 51.2 mmol) in 6 mL of acetic acid was added drop wise and stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in methylene chloride. The reaction mixture neutralized by saturated aq. NaHCO3 solution and the organic phase was separated from the aqueous phase. The aqueous phase extracted with methylene chloride and the combined organic layers was dried over sodium sulfate, concentrated and the residue was purified by silica column using hexanes and ethyl acetate as eluent to give 1.85 g of title compound.

Provenance & Evidence