2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67163785, compound

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Reaction Conditions

Reaction Steps

(6-chloro-1,3,4,9-tetrahydro-β-carbolin-2-yl)-phenyl-methanone (1.76 g, 5.66 mmol, 1 equiv.) and DDQ (2.31 g, 10.2 mmol, 1.8 equiv.) were mixed as solids and cooled to −78° C. 15 ml of a 9:1 THF/H2O solution was cooled to −78° C. and the resulting slurry was added to the cooled solids followed by an additional 15 ml of THF (also cooled to −78° C.). The deep blue solution was stirred at −78° C. for 2 hours and then gradually warmed to room temperature and stirred an additional two hours. The reaction was quenched by the addition of 1 N NaOH, and extracted with 3×150 ml EtOAc. The combined organic layers were washed with 2×100 ml 1 N HCl, 1×100 ml brine, dried over MgSO4, filtered and concentrated to yield 1.38 g (75%) of 2-benzoyl-6-chloro-1,2,3,9-tetrahydro-β-carbolin-4-one as oily orange solids. 1H-NMR (300 MHz, DMSO-d6): δ 12.11-12.48 (br, 1H), 7.29-7.88 (m, 8H), 4.93-5.18 (br, 2H), 4.60-4.46 (br, 2H). Exact Mass: 324.07. Formic acid standard conditions. DAD RT=2.15 min. M+H=325.

Provenance & Evidence