Synthesis of several 2,7-dibromoacridine derivatives, including 4-[2-(succinimidyloxycarbonyl)ethyl]phenyl 2,7-dibromo-10-methylacridinium-9-carboxylate trifluoromethanesulfonate

Smith, Keith and El-Hiti, Gamal A. ORCID: https://orcid.org/0000-0001-6675-3126 2024. Synthesis of several 2,7-dibromoacridine derivatives, including 4-[2-(succinimidyloxycarbonyl)ethyl]phenyl 2,7-dibromo-10-methylacridinium-9-carboxylate trifluoromethanesulfonate. ARKIVOC 2024 (1) , 202412307. 10.24820/ark.5550190.p012.307

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Abstract

The reaction of bis(4-bromophenyl)amine and oxalyl chloride gave N-(4-bromophenyl)-5-bromoisatin, which on treatment with potassium hydroxide yielded 2,7-dibromoacridine-9-carboxylic acid. Treatment of acridine- 9-carboxylic acid with freshly redistilled thionyl chloride followed by reaction with benzyl 3-(4- hydroxyphenyl)propanoate gave the corresponding benzyl ester. Hydrolysis of the benzyl ester gave the corresponding acid, which, on reaction with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide, gave the corresponding ester. Finally, methylation of the N-hydroxysuccinimide ester gave the corresponding 10-methylacridinium trifluoromethanesulfonate.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry
Publisher:	ARKAT USA
ISSN:	1551-7012
Date of First Compliant Deposit:	3 January 2025
Date of Acceptance:	3 December 2024
Last Modified:	29 Jan 2025 12:18
URI:	https://orca.cardiff.ac.uk/id/eprint/174977

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