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Direct Amination of 9-Hydroxy-1-oxophenalene to Produce 9-Amino-1-oxophenalene and Related Compounds

Haddon, R. C. and Chichester, S. V. and Mayo, Stephen L. (1985) Direct Amination of 9-Hydroxy-1-oxophenalene to Produce 9-Amino-1-oxophenalene and Related Compounds. Synthesis-Stuttgart, 1985 (6-7). pp. 639-641. ISSN 0039-7881 . http://resolver.caltech.edu/CaltechAUTHORS:20110928-141129059

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Abstract

In connection with our studies of organo-non-metallic complexes of the 1,9-disubstituted phenalene unit 1 we required access to compounds possessing a total of just two ionizable hydrogen atoms in the A,B groups of 1. The prototypical compound in this series, 9-amino-1-oxophenalene (2), is not known although 9-hydroxy-l-oxophenalene (3) was first prepared in 1941 and a number of derivatives of 1 possessing one or three ionizable hydrogen atoms in the A,B groups have recently become available. We have found that the high-pressure reaction between 9-hydroxy-1-oxophenalene (3) and aqueous ammonia affords the desired 9-amino-1-oxophenalene (2) in high yield and good purity under relatively mild conditions. In addition 2 may be alkylated to produce the 9-amino-l-ethoxyphenalenylium salt which serves as a precursor for the other derivatives in this series with two ionizable hydrogen atoms in the A,B groups of 1.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1055/s-1985-34145DOIUNSPECIFIED
https://www.thieme-connect.de/DOI/DOI?10.1055/s-1985-34145PublisherUNSPECIFIED
Additional Information:© 1985 Georg Thieme Verlag. Received: October 29, 1984. Revised form: December 12, 1984.
Record Number:CaltechAUTHORS:20110928-141129059
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20110928-141129059
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:25475
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:06 Oct 2011 20:06
Last Modified:06 Oct 2011 20:06

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