- PROCESS FOR THE PREPARATION OF AQ4N
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A process for the preparation of compound AQ4N of formula (2) or a salt or solvate thereof wherein the said process includes the reaction step: Formula (1), Formula (2), where compound AQ4 of formula (1) is oxidised to compound AQ4N of formula (2) with an oxidising agent at a reaction temperature not exceeding 10°C.
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Page/Page column title page; 17; 20
(2008/06/13)
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- A large-scale synthesis of the bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide (AQ4N)
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A large-scale synthesis of the bis-bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxy-anthracene-9,10-dione bis-N-oxide (AQ4N) has been developed. This six-step synthesis provides AQ4N in 20% overall yield from readily available tetrachlorophthalic anhydride. The key step was a KF-NaF-mediated conversion of 3,6-dichlorophthalic anhydride to 3,6-difluorophthalic anhydride, which could be achieved in 77% yield on a 100 g scale. A trace impurity in AQ4N was determined (by LC-MS and independent synthesis) to be the mono-N-oxide 1-amino-4-[2-(dimethylamino)ethyl]amino-5,8-dihydroxyanthracene-9,10-dione N-oxide. This is formed spontaneously from AQ4N under a number of conditions, including during HPLC on reversed-phase columns. The Royal Society of Chemistry 1999.
- Lee, Ho H.,Denny, William A.
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p. 2755 - 2758
(2007/10/03)
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