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7-amino-2-pyrenecarboxylic acid

Authors: 
Abdallah Musa, Bhama Sridharan, Hyoyoung Lee, and Daniell Lewis Matter
Journal Name: 
J. Org. Chem
Volume: 
61
Issue: 
11
Pages From: 
5481
To: 
5484
Date: 
Thursday, May 16, 1996
Abstract: 
Pyrenes undergo initial electrophilic substitution in the 1 position; a second substitution typically occurs in the 3, 6, or 8 positions. We sought a pyrene with synthetically useful handles in the unusual 2,7 substitution pattern. To that end, 7-amino-2-pyrenecarboxylic acid was prepared by partial reduction of pyrene to 4,5,9,10-tetrahydropyrene, Friedel-Crafts acylation in the 2 position, and conversion to 2-carbethoxytetrahydropyrene through the haloform reaction and esterification. Nitration of the ester proceeded in the 7 position; rearomatization, reduction of the nitro group, and saponification gave the title compound.