PROCESS FOR PREPARING (E)-(5,6-DIHYDRO-1,4,2-DIOXAZINE-3-YL) (2-HYDROXYPHENYL) METHANONE O-METHYL OXIME

A process for preparing (E)-(5,6-dihydro-l,4,2-dioxazin-3-yl)(2- hydroxyphenyl)methanone O-methyl oxime is described which includes: (i) reacting benzofuran-3(2H)-one O-methyl oxime (1) with at least one nitrite selected from n-butyl nitrite and tert-butyl nitrite, in the presence of a metal alkoxid...

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Main Authors SRIKANTH, A., Sai, RAVIKUMAR, K. N, RAO, Sampadarao, Ananda, GIBB, Cameron, PRASAD, Vic, PAWAR, Jivan, Dhanraj, MANE, Avinash, Shesharo, BALAKRISHNAN, Sankar, LARSON, Christopher, Lynn, SATEESH, Sagi
Format Patent
LanguageEnglish
French
Published 08.12.2016
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Summary:A process for preparing (E)-(5,6-dihydro-l,4,2-dioxazin-3-yl)(2- hydroxyphenyl)methanone O-methyl oxime is described which includes: (i) reacting benzofuran-3(2H)-one O-methyl oxime (1) with at least one nitrite selected from n-butyl nitrite and tert-butyl nitrite, in the presence of a metal alkoxide to form (2Z,32)-2,3-benzofuran-dione O3-methyl dioxime (2) as the predominant isomer; (ii) reacting the (2Z,3Z)-2,3-benzofuran-dione O -methyl dioxime (2) with 2- haloethanol to form (2Z,3Z)-benzofuran-2,3-dione 02-(2-hydroxyethyl) O3 -methyl dioxime (3); and (iii) reacting the (2Z,3Z)-benzofuran-2,3-dione 02-(2-hydroxyethyl) & -methyl dioxime (3) with an acid to form (E)-(5,6-dihydro-l,4,2-dioxazin-3-yl)(2- hydroxyphenyl)methanone (9-methyl oxime (4); L'invention concerne un procédé de préparation de O-méthyl-oxime de (E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphényl)méthanone qui comprend : (i) la réaction de O-méthyl-oxime de benzofuran-3(2H)-one (1) avec au moins un nitrite choisi parmi le nitrite de n-butyle et le nitrite de tert-butyle, en présence d'un alcoxyde métallique pour former la O-méthyl dioxime de (2Z,3Z)-2,3-benzofurane-dione (2) comme isomère principal ; (ii) la réaction de la O-méthyl dioxime de (2Z,3Z)-2,3-benzofurane-dione (2) avec du 2-halogénoéthanol pour former de la 2-(2-hydroxyéthyl) O-méthyl dioxime de (2Z,3Z)-benzofurane-2,3-dione (3) ; et (iii) la réaction de la 2-(2-hydroxyéthyl) O-méthyl dioxime de (2Z,3Z)-benzofurane-2,3-dione (3) avec un acide pour former de la O-méthyl-oxime de (E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphényl)méthanone (4).
Bibliography:Application Number: WO2016IB00871