Medroxalol

Medroxalol

Identifiers
IUPAC name 5-(2-{[4-(1,3-Benzodioxol-5-yl)-2-butanyl]amino}-1-hydroxyethyl)-2-hydroxybenzamide
CAS Number	56290-94-9
PubChem (CID)	41835
ChemSpider	38173
ECHA InfoCard	100.054.618
Chemical and physical data
Formula	C20H24N2O5
Molar mass	372.415 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N)c1cc(ccc1O)C(O)CNC(C)CCc2ccc3OCOc3c2
InChI InChI=1S/C20H24N2O5/c1-12(2-3-13-4-7-18-19(8-13)27-11-26-18)22-10-17(24)14-5-6-16(23)15(9-14)20(21)25/h4-9,12,17,22-24H,2-3,10-11H2,1H3,(H2,21,25) Key:MPQWSYJGFLADEW-UHFFFAOYSA-N

Medroxalol is a vasodilator beta blocker also classified as a mixed receptor blocker as it blocks both alpha and beta receptors.

Synthesis

Medroxalol synthesis:^[1]

For the first step, salicylamide (1) is the subject of a Friedel-Crafts acetylation and then the aromatic methylketone 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

Labetalol

References

1. J. T. Suh and T. M. Bare, U.S. Patent 3,883,560; Chem.Abstr. 83, 78914J (1975).