Sodium Hydroxide → HCID 9796768, compound

Participants

Reaction Steps

To a degassed solution of 1500 ml of absolute ethanol and 510 ml of 2N NaOH (1.02 mol) is added 150 g (0.51 mol) of N-(2′-chloro-4′,6′-difluorophenyl)-5-methyloxindole. The resultant mixture is degassed and heated to 60-65° for 2 hours. Most of the ethanol is removed under reduced pressure and then 4500 ml of water is added to the residue which is then washed three times with 1500 ml of toluene. The aqueous layer is cooled to 0° and adjusted to pH 6 using 1.2 N HCl. The solid is filtered off and washed with 100 ml of water and dried. Recrystallization from ethyl acetate and heptane gives 5-methyl-2-(2′,4′-difluoro-6-chloroanilino)phenylacetic acid of Example 1(g).

Provenance & Evidence