2-chloro-N-(3-methoxyphenyl)acetamide → 6-hydroxy-2,3-dihydro-1H-indol-2-one

Participants

Reaction Conditions

Reaction Steps

2-chloro-N-(3-methoxyphenyl)acetamide (3.1 g, 16 mmol) and anhydrous AlCl3 powder (4.4 g, 32 mmol) is heated and stirred at 120° C. for 10 minutes and exhibit a melting state. The temperature is elevated gradually to 240° C. in 40 minutes and then stirred 5 minutes. The reaction is allowed to cool to obtain a brown powder. The solid powder is poured into a mixture of 100 g of crushed ice and 50 ml of concentrated hydrochloric acid. The mixture is stirred for 10 minutes and then reflux for 10 minutes, and allowed to cool to precipitate a light yellow powder, which is filtered out and recrystallized in water to obtain 1.5 g of 6-hydroxy-indoline-2-one, with a yield of 62%.

Provenance & Evidence