2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19095280, compound

Participants

Reaction Conditions

Reaction Steps

N-[2-(4,5-Dihydro-1H-benzo[g]indol-1-yl)ethyl]acetamide (4.0 g) was dissolved in 50 ml of toluene under argon and treated with 3.8 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The reaction mixture was stirred at 80° C. for 2 hours, a further 0.4 g of DDQ was then added and the mixture was stirred at 80° C. for a further 2 hours. The separated precipitate was filtered off at room temperature and the filtrate was freed from solvent. The crude product, 1.5 g of dark brown solid, was chromatographed on 60 g of neutral aluminium oxide with ethyl acetate as the eluent. There were obtained 1.2 g (30%) of N-[2-(1H-benzo[g]indol-1-yl)ethyl]acet-amide which was processed without further purification.

Provenance & Evidence