Preparation and uses of n-methylnitrone

Details Preparation and uses of n-methylnitrone Preparation and uses of n-methylnitrone

C - Chemistry, Metallurgy

07

C

C07C 213/06 (2006.01) C07C 213/08 (2006.01) C07C 239/10 (2006.01) C07C 291/02 (2006.01) C07D 261/02 (2006.01) C07C 215/08 (2006.01) C07C 217/20 (2006.01)

Patent

CA 2293472

Oxidation of secondary amines with hydrogen peroxide and sodium tungstate is reported to give good yields of nitrones. However, when using dimethylamine in this manner, a considerable amount of N,N-dimethylformamide was produced as a co-product. To more selctively produce N-methylnitrone from dimethylamine, a two-step process is used which comprises (a) mixing together dimethylamine and a peroxidic compound, and subjecting the resultant mixture to reaction conditions effective to form a reaction mixture in which N,N- dimethylhydroxylamine has been formed; and (b) mixing together (i) reaction mixture from (a), (ii) a peroxidic compound, and (iii) a transition metal- containing oxidation catalyst, and subjecting the resultant mixture to reaction conditions effective to form a reaction mixture in which N- methylnitrone has been formed. Highest yields of N-methylnitrone are achieved by conducting step (b) at a pH in the range of 7 to 12, and at a temperature in the range of -10 to 100 ~C.

L'oxydation d'amines secondaires effectuée à l'aide de peroxyde d'hydrogène et de tungstate de sodium permet d'obtenir de bons rendements de nitrones. Cependant, lorsqu'on utilise la diméthylamine de cette manière, une quantité importante de N,N-diméthylformamide est produite comme coproduit. Afin de produire de façon plus sélective de la N-méthylnitrone à partir de diméthylamine, on a recours à un procédé en deux étapes, lesquelles consistent à: (a) mélanger une diméthylamine et un composé peroxyde, et soumettre le mélange obtenu à des conditions de réaction efficaces pour former un mélange réactionnel dans lequel de la N,N-diméthylhydroxylamine est formée; et (b) mélanger (1) le mélange réactionnel obtenu en (a), (2) un composé peroxyde et (3) un catalyseur d'oxydation renfermant un métal de transition; et soumettre le mélange obtenu à des conditions de réaction efficaces pour former un mélange réactionnel dans lequel de la N-méthylnitrone est formée. On obtient les plus grands rendements de N-méthylnitrone en mettant en oeuvre l'étape (b) dans des conditions de pH de l'ordre de 7 à 12, et à une température comprise entre -10 et 100 ·C.

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