Hydrochloric Acid → 5-Chloro-3-hydroxy-3-(2-methoxy-6-methylphenyl)-1,3-dihydro-2H-indol-2-one

Participants

Reaction Steps

A solution of 2-methoxy-6-methylphenyl-magnesium bromide is prepared starting with 2.2 g of magnesium in 10 ml of THF and a solution of 16 g of 1-bromo-2-methoxy-6-methylbenzene in 40 ml of THF. This solution is added dropwise at RT to a mixture of 6 g of 5-chloro-1H-indole-2,3-dione in 50 ml of THF and the resulting mixture is then refluxed for 1 hour. After cooling to RT, the reaction mixture is poured into 200 ml of 3N HCl solution and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. 5.7 g of the expected product are obtained after crystallization from iso ether.

Provenance & Evidence