Benzoyl chloride, 3-nitro- → 5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one

Participants

Reaction Conditions

Reaction Steps

A 3 L, 3 necked round bottomed flask equipped with a mechanical stirrer, thermocouple and was charged with AlCl3 (256 g, 1.92 mol). The solids were cooled to 0° C. with an ice-H2O bath. DMF (42 ml) was added dropwise over a period of 35 min. The temperature was stirred at 0° C. for 2 h then was warmed to room temperature. The reaction mixture was treated with 3-Nitrobenzoyl chloride (37.3 g, 0.2 mol) and the resulting slurry was heated to 41° C. Subsequently, oxindole (25 g, 0.19 mol) was added over a period of 10 min. The reaction that ensued was exothermic and caused the internal reaction temperature to rise to 60° C. The reaction was heated at 90° C. for 3.5 h. Thin layer chromatographic analysis (Hexanes/ethylacetate 1:1) indicated completion of reaction. The reaction was cooled and ice-H2O (1.5 L) was added dropwise over a period of 1.5 h. The solids were filtered, washed with saturated NaHCO3(aq) (2×300 mL), H2O (300 mL) and Methyl-t-Butyl Ether (500 mL) to yield 5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one in quantitative yield (53.63 g, 0.19 mol).

Provenance & Evidence