Hydrochloric Acid → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

Participants

Reaction Conditions

Reaction Steps

Under ice-cooling, aluminum chloride (anhydride) (3.5 equivalents) was suspended in methylene chloride, and oxindole (1 equivalent) was added to this solution while stirring. To this solution, chioroacetyl chloride (2 equivalents) was gradually added dropwise, and after generation of hydrogen chloride gas was stopped, the resulting mixture was stirred for about 10 minutes. Thereafter, the reaction mixture was warmed to 40 to 50° C. and stirred for 2 hours. After cooling, the reaction mixture was poured into ice water and the resulting precipitate was collected by filtration, washed with water and dried, whereby 5-chloroacetylindolin-2-one was obtained. 5-chloroacetylindolin-2-one was dissolved in pyridine and the resulting mixture was heated and stirred at 80 to 90° C. for 3 hours. After cooling, the resulting precipitate was collected by filtration, washed with ethanol several times and dissolved in 2.5 N sodium hydroxide, and the resulting solution was stirred at 70 to 75° C. After cooling, the reaction mixture was acidified with hydrochloric acid and the resulting precipitate was collected by filtration, washed with water and dried, whereby 5-carboxyindolin-2-one was obtained. From the thus obtained 5-carboxyindolin-2-one and diformylfuran, a target compound was obtained in the same manner as in Example 1.

Provenance & Evidence