Medroxalol
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| File:Medroxalol.svg | |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
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| E number | {{#property:P628}} |
| CompTox Dashboard (EPA) |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C20H24N2O5 |
| Molar mass | 372.421 g·mol−1 |
| 3D model (JSmol) | |
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Medroxalol is a vasodilator beta blocker also classified as a mixed receptor blocker as it blocks both alpha and beta receptors.[1]
Synthesis
[edit | edit source]
For the first step, salicylamide (1) is the subject of a Friedel-Crafts acetylation and then the aromatic methyl ketone is halogenated. in the usual manner. The bromide in 2 is then displaced by the nitrogen in N-benzyl-1-(3',4'-methylenedioxyphenyl)-3-butylamine (3), which is itself prepared by reductive amination on the corresponding ketone. The product of the last step (4) is catalytically hydrogenated. This serves the dual purpose both of reducing the ketone and removing the benzyl protecting group affording the product medroxalol (5). Note that a benzyl protecting group is not necessarily used.
See also
[edit | edit source]References
[edit | edit source]- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ J. T. Suh and T. M. Bare, U.S. patent 3,883,560; Chem.Abstr. 83, 78914J (1975).
