Synthesis
3-Amino-2-(4-methoxyphenyl)-1-indanone was added to 20% sulfuric acid in water. The multiphase mixture was refluxed. After about half an hour, the deep red color disappeared, and a white solid was visible. The solid was extracted three times with dichloromethane, washed with deionized water, and then washed with a brine solution. It was then dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was usually recrystallized from anhydrous ethanol to give a white compound.
Chemical Properties
Slightly beige or yellow powder
Originator
Miradon,Schering,US,1960
Uses
Anisindione is a synthetic anticoagulant that prevents the formation of active procoagulation factors and proteins in the liver.
Definition
ChEBI: A cyclic beta-diketone consisting of indane-1,3-dione having a 4-methoxyphenyl substituent at the 4-position.
Manufacturing Process
To a hot solution of 20.6 g of sodium in 400 ml of absolute ethanol, there is
added a solution of 110 g of phthalide and 110 g of p-methoxybenzaldehyde.
A vigorous reaction ensues and one-half of the alcohol is distilled off over a
two hour period. Ice and water are added to the red solution and the diluted
solution is acidified with hydrochloric acid. The resulting gum solidifies and the
aqueous phase is removed by decantation. The crude solid is recrystallized
twice from two liters of ethanol yielding 2-(p-methoxyphenyl)-1,3-indandione
as pale yellow crystals, MP 155-156°C.
brand name
Miradon (Schering).
Therapeutic Function
Anticoagulant
General Description
Anisindione, 2-(p-methoxyphenyl)-1,3-indandione, 2-(p-anisyl)-1,3-indandione (Miradon), is ap-methoxy congener of phenindione. It is a white, crystallinepowder, slightly soluble in water, tasteless, and absorbedwell after oral administration.
In instances when the urine may be alkaline, an orangecolor may be detected. This is caused by metabolic productsof anisindione and is not hematuria.
Purification Methods
Crystallise anisidinone from acetic acid or EtOH. [Horeau & Jacqius Bull Soc Chim Fr 53 1948, Koelsch J Am Chem. Soc 58 1331 1936, Beilstein 8 III 2931.]
