Phthalic Anhydride → HCID 615346, compound

Participants

Reaction Steps

Referring to the above equations, the starting 8-aminoquinoline I was treated with phthalic anhydride to give the 8-phthalimidoquinoline II. This was necessary to provide protection for the 8-amino group during peroxidation and introduction of the 2-chloro group. Thus compound II was treated with MCPBA, followed by chromatography over basic alumina to afford the 1-oxide III. Intermediate III was treated directly (preferred procedure) with phosphorus oxychloride to afford the 2-chloro derivative V. However, it was discovered also that treatment of the reaction mixture from the oxidation step with a combination of basic and neutral alumina gave the 2-quinolone IV which was converted also with phosphorus oxychloride to give the 2-chloro derivative V, albeit in lower yield.

Provenance & Evidence