2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19420953, compound

Participants

Reaction Steps

A solution of 0.86 g (3.34 mmol) of (RS)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indazol-1-yl)-1-methyl-ethylamine, 0.56 ml (4 mmol) of triethylamine and 0.56 ml (4 mmol) of ethyl trifluoroacetate in 60 ml of anhydrous methanol was stirred at room temperature for 50 hours. After removing the solvent in a vacuum, the residue was taken up with 70 ml of anhydrous dioxan, 0.8 g (3.5 mmol) of DDQ was added and the mixture was boiled under reflux for 3 hours. Subsequently, the reaction mixture was concentrated in a vacuum and the residue was purified by column chromatography on silica gel (dichloromethane/acetone 4:1). 0.97 g (82%) of (RS)-N-[2-(8-methoxy-1H-benz[g]indazol-1-yl)-1-methyl-ethyl]-trifluoroacetamide was obtained as a pale brown solid which was used in the next reaction without further recrystallization.

Provenance & Evidence