Water → HCID 21710156, compound

Participants

Reaction Steps

A stirred mixture of 5.0 grams (0.022 mole) of 2-(1-methylethyl)-4-nitroisoindolin-1-one and 10 mL of water in 100 mL of HOAc was warmed to 50 C., and 5.0 grams of iron dust was slowly added. Upon completion of addition, the reaction mixture was stirred at 25 C. for about two hours, then it was filtered through diatomaceous earth. The filtrate was diluted with water and extracted with EtOAc. The organic layer was separated and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel using mixtures of EtOAc and methylene chloride as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding 3.6 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence