ChemicalBook CAS DataBase List Aminoglutethimide

Aminoglutethimide synthesis

6synthesis methods

Product Name:Aminoglutethimide
CAS Number:125-84-8
Molecular formula:C13H16N2O2
Molecular Weight:232.28

Aminoglutethimide, (±)-2-(4-aminophenyl)-2-ethylglutarimide (30.5.4), is made by two methods, the first of which begins with glutethimide (4.3.6), which is nitrated to form 2-(4-nitrophenyl)-2-ethylglutarimide (30.5.3). Reducing the nitro group with hydrogen over a nickel catalyst gives the desired aminoglutethimide (30.5.4).

The second method starts with 2-phenylbutyronitrile, which is nitrated under analogous conditions, forming 2-(4-nitrophenyl)butyronitrile (30.5.5). The last, in Michael addition reaction conditions, in the presence of benzyltrimethylammonia hydroxide is added to methylacrylate, and the obtained product undergoes acidic hydrolysis by a mixture of acetic and sulfuric acids, during which a cyclyzation to 2-(4-nitrophenyl)-2-ethylglutarimide (30.5.3) occurs, and this product is reduced by hydrogen by the analogy to that described above, to give the desired product aminoglutethimide (30.5.4) .