4H-Pyrrolo[3,2,1-ij]quinolin-6(5H)-one synthesis

Yield:603310-86-7 25.8%

Reaction Conditions:

with 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane at 20; for 3 h;

Steps:

180

Oxidation; Add DDQ (5.9 g, 26.0 mmol) to 1, 2,5, 6-tetrahydropyrrolo [3,2, 1-ij] quinolin-6-one (1.8 g, 10.4 mmol) in dioxane (40 mL) and stir at room temperature for 3 hours. Partition the reaction mixture between ethyl acetate (200 mL) and 1N sodium hydroxide (100 mL) with ice. Wash the organic phase with water (100 mL) and saturated aqueous sodium chloride. Dry over sodium sulfate and concentrate under reduced pressure. Subject the residue to chromatography, eluting with ethyl acetate/hexanes (1: 1) to provide the title compound (460 mg, 25.8 %) as a pale yellow solid.

References:

WO2003/76442,2003,A1 Location in patent:Page/Page column 85