Acetic Anhydride → HCID 20272390, compound

Participants

Reaction Steps

The product aniline of Example 31 was acetylated at room temperature using 8.2 ml (86.6 mmole) of acetic anhydride in 100 ml of pyridine. After one day the mixture was concentrated in vacuo to a syrup which afforded a solid upon trituration with water. The solid was collected, washed with water, and dried under vacuum at 40°, giving 4.8 g (16.3 mmole) of 2-phthalimido-5-acetamidotoluene. The intermediate compound was heated at reflux in 100 ml of ethanol containing 3.2 ml (65.2 mmole) of hydrazine hydrate. After 45 minutes the mixture was filtered and the filtrate was concentrated to dryness. The crude amine was used in subsequent reactions without further purification.

Provenance & Evidence