Dimethylformamide → 6-Dipropylamino-1,5,6,7-tetrahydro-1-aza-s-indacen-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of dipropyl-(1,5,6,7-tetrahydro-1-aza-s-indacen-6-yl)amine (100 mg, 0.39 mmol) in dimethyl formamide (5 mL) was added to a solution of phosphorous oxychloride (200 μL, 329 mg, 2.14 mmol) in dimethyl formamide (5 mL) at -5° C. The mixture was heated at 50° C for 2 hours, poured on ice and treated with 5M sodium hydroxide and heated again for 20 minutes. After cooling, the mixture was extracted using dichloromethane. The combined organic extracts were dried (magnesium sulfate), filtered and evaporated to yield a residue of 70 mg, which was purified on silica using methanol as eluant, yielding 33 mg (30%) of the pure compound as an oil.:

Provenance & Evidence