Reacción #657349

ord-a369aaa1b46948c3b632be5438e216a0

Ecuación de reacción

COc1ccc(N)c(C(=O)O)c1
5-methoxyanthranilic acid
CC(=O)OC(C)=O
acetic anhydride
COc1ccc2nc(C)oc(=O)c2c1
title compound
Rendimiento 77.0%
COc1ccc2nc(C)oc(=O)c2c1
2-methyl-6-(methyloxy)-4H-3,1-benzoxazin-4-one
Rendimiento 77.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturabefore being cooled
  2. 2
    Concentraciónconcentrated under reduced pressure
  3. 3
    ConcentraciónThe crude residue was then concentrated twice in the presence of toluene
  4. 4
    Filtraciónbefore being filtered
  5. 5
    Lavadowashed with ether

Procedimiento

A solution of 5-methoxyanthranilic acid (7.8 g, 46.5 mmol) was refluxed in acetic anhydride (60 mL) for 2 h15 before being cooled and concentrated under reduced pressure. The crude residue was then concentrated twice in the presence of toluene before being filtered and washed with ether to yield to the title compound (6.8 g, 77% yield) as a beige solid; LC/MS: m/z 192 [M+H]+, Rt 1.69 min.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09023842B2uspto-grants-2015_05