3-Methylglutaric acid → 8-chloro-3-methyl-2,3,4,4a-tetrahydro-10H-1,2-oxazino(3,2-b) (1,3)benzoxazin-10-one

HRID 2398048

Reaktionsgleichung

Reaktionsgleichung von HRID 2398048
CC(CC(O)=O)CC(O)=O.Br[CH2:12][CH:13]([CH3:19])[CH2:14][C:15]([O:17][CH3:18])=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-].BrCC(C)CC=O.[Cl:41][C:42]1[CH:51]=[C:46]([C:47]([NH:49][OH:50])=[O:48])C(O)=[CH:44][CH:43]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.CCOCC>[Cl:41][C:42]1[CH:43]=[CH:44][C:18]2[O:17][CH:15]3[CH2:14][CH:13]([CH3:19])[CH2:12][O:50][N:49]3[C:47](=[O:48])[C:46]=2[CH:51]=1

Komponenten

9

Edukt 6

HCID 122843-Methylglutaric acidHCID 14798Sodium HydroxideHCID 169935Benzamide, 5-chloro-N,2-dihydroxy-HCID 123659514-Bromo-3-methylbutanalHCID 14104192Methyl 4-bromo-3-methylbutanoateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Produkt 1

HCID 123659528-chloro-3-methyl-2,3,4,4a-tetrahydro-10H-1,2-oxazino(3,2-b) (1,3)benzoxazin-10-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

80 g. of the methyl half ester of 3-methylglutaric acid (Linstead, lunt and Weedon, J. Chem. Soc. 1950, 3331) was converted to methyl 4-bromo-3-methylbutyrate as described by Marks and Polgar, J. Chem. Soc. 1955, 3854. The bromoester (51 g.) was reduced with sodium bis (2-methoxyethoxy)aluminum hydride in a mixture of toluene and ether yielding 43 g. of 4-bromo-3-methylbutyraldehyde. The aldehyde and 49 g. of 5-chlorosalicylhydroxamic acid were condensed by the method described in Example 1 and the product was ring-closed with 10 percent aqueous sodium hydroxide to give 8-chloro-3-methyl-2,3,4,4a-tetrahydro-10H-1,2-oxazino(3,2-b) (1,3)benzoxazin-10-one which melted at 121- 140° C. after recrystallization from ethanol.

Aufarbeitung

  1. customcondensed by the method

Quellen und Nachweise

ORD-Eintrag
ord-fa4ec6789782446eb9b285e8d9dde42e
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04024139

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