2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59467517, compound

Participants

Reaction Conditions

Reaction Steps

1.0 g benzo[c][1,5]naphthyridine (5.5 mmol) was dissolved in 30 mL tetrahydrofuran (THF) and then cooled to −78° C. under nitrogen with stirring. 4.4 mL methyl lithium (MeLi) (6.6 mmol, 1.5M) was added and reacted for 1 hr. After quenching the reaction by a saturated ammonium chloride (NH4Cl) solution, extraction by ethyl acetate, drying, and concentration, 30 mL THF and 1.87 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (8.2 mmol) were added and reacted for 8 hr. After extraction by ethyl acetate, drying, concentration, and purification by silicon-gel column, 0.83 g light yellow solid was obtained, with a yield of 77%.

Provenance & Evidence