2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86647176, compound

Participants

Reaction Steps

6-Chloro-N-methylnicotinamide (2.00 g, 11.7 mol) was dissolved in tetrahydrofuran (59 mL), added propylmagnesium bromide (46.9 mL, 46.9 mol) under ice-cold conditions, and stirred at room temperature for 4.5 hours. Then, propylmagnesium bromide (46.9 mL, 46.9 mol) was added under ice-cold conditions and the mixture was further stirred at room temperature for 9 hours. The reaction solution was added methanol (140 mL) and ammonium chloride (7.5 g) under ice-cold conditions, and stirred at room temperature for 0.5 hours. The reaction solution was added DDQ (3.19 g, 14.1 mmol) under ice-cold conditions, and stirred at room temperature for 2 hours. The reaction solution was added tert-butyl methylether, and filtered through a pad of celite, concentrated in vacuo, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (chloroform/methanol). The title compound (1.88 g (yield 75%)) was obtained as a light brown crystal.

Provenance & Evidence