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9‐Substituted acridines. Demethoxylation of 9‐methoxyacridine and dechlorination of 9‐chloroacridine in hydroxylic solvents
Author(s) -
Kalatzis Evangelos,
Konga Zoi,
Geronikolou Konstantina
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330366
Subject(s) - chemistry , sodium hydroxide , potassium hydroxide , perchlorate , methanol , methoxide , hydrochloric acid , perchloric acid , sodium methoxide , sodium perchlorate , sodium , protonation , inorganic chemistry , organic chemistry , medicinal chemistry , ion , electrode , electrochemistry
In methanol‐water mixtures containing sodium or potassium hydroxide (up to 2.00 M ) the demethoxylation of 9‐methoxyacridine to 9‐acridone is of first order in both the free form of 9‐methoxyacridine and the hydroxyl ion. The rate of the reaction is increased with an increase in the concentration of water. Sodium perchlorate has a small retarding effect on the reaction. In methanol‐water mixtures containing perchloric or hydrochloric acid (up to 3.45 M ) the demethoxylation is of first order with respect to the protonated form of 9‐methoxyacridine. The rate of the reaction decreases with an increase in the concentration of the acid or of sodium perchlorate, but when the concentration of water is increased (≈1.7 to 50 M ) and that of the acid is not changed, it reaches a maximum value in mixtures containing 8 to 10 M ‐water. The dechlorination of 9‐chloroacridine to 9‐methoxyacridine in methanol containing sodium hydroxide or methoxide (up to 0.31 M ) is of first order in both the 9‐chloroacridine and the hydroxyl or methoxyl ions.