Chlorosuccinimide → 2-Chloro-3-(3-cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one

Participants

Reaction Steps

To a solution 0.49 g (1.69 mmole) of the 3-(3-cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one produced in Example 1(3) in 5 ml of an ethanol-water (9:1) solution was added 0.25 g (1.86 mmole) of N-chlorosuccinimide. The mixture was stirred at room temperature for 1.5 hours. After the reaction, the solvent was removed in vacuo. Next, the residue obtained was diluted with 100 ml of ethyl acetate and the solution was successively washed with a saturated sodium hydrogencarbonate solution and brine. The organic solution was dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo to obtain a crude product as a black oil. The crude product obtained here was purified by flash chromatography. The solvent was removed and the residue dried in vacuo to obtain the title compound 0.45 g (yield 82.5%) as a light pink solid.

Provenance & Evidence