Phthalic Anhydride → HCID 615346, compound

HRID 2290651Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>>[C:12]1(=[O:17])[N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12

Participants

Reactant 2

HCID 6811Phthalic Anhydride

HCID 113598-Aminoquinoline

Product 1

HCID 615346HCID 615346, compound

Procedure

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.

Sources & evidence

ORD record: ord-767f6f9033914cce977e99064030ae59
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04617394

Reaction notes

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