O-(propan-2-yl)hydroxylamine hydrochloride → HCID 67506941, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a mixture of N-(4-chloroquinolin-3-yl)trimethylacetamide (6.00 g, 1 eq), O-isopropylhydroxylamine hydrochloride (7.6 g, 3 eq), and anhydrous isopropanol (80 mL) was heated at 80° C. for 19 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed sequentially with saturated aqueous potassium carbonate, water, and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by column chromatography (150 g of silica gel eluted with a gradient of 20-55% ethyl acetate in dichloromethane) to provide 2.8 g of 2-tert-butyl-1-isopropoxy-1H-imidazo[4,5-c]quinoline as a brown oil.

Provenance & Evidence