Acetic Anhydride → 6-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one

HRID 82014

Reaktionsgleichung

Reaktionsgleichung von HRID 82014
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([NH2:12])=[CH:5][CH:4]=1.[C:13](OC(=O)C)(=O)[CH3:14]>>[CH3:13][C:14]1[O:9][C:8](=[O:10])[C:7]2[CH:11]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N:12]=1

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 2779305-Methoxyanthranilic acid

Produkt 1

HCID 6055556-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-oneAusbeute 71 %

Versuchsvorschrift

A solution of 5-methoxyanthranilic acid (Lancaster) (41.8 g, 0.25 mol) was refluxed in acetic anhydride (230 ml) for 3.5 h before being concentrated under reduced pressure. The crude compound was then concentrated twice in the presence of toluene before being filtered and washed twice with ether to yield to the title compound (33.7 g, 71% yield) as a brown solid; LC/MS (Method D): m/z 192 [M+H]+, Rt 1.69 min.

Aufarbeitung

  1. concentrationbefore being concentrated under reduced pressure
  2. concentrationThe crude compound was then concentrated twice in the presence of toluene
  3. filtrationbefore being filtered
  4. washwashed twice with ether

Quellen und Nachweise

ORD-Eintrag
ord-3819c297d3444699901c9320d2b76f5d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846709B2

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