Water → 5,7-Dimethoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one

HRID 130327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130327
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:14])[C:6](=[C:10]([O:12][CH3:13])[CH:11]=1)[C:7]([OH:9])=[O:8].[CH2:15](N(CC)CC)[CH3:16].C(OC(=O)C)(=O)C.O>C(Cl)Cl>[CH3:13][O:12][C:10]1[C:6]2[C:7](=[O:9])[O:8][C:15]([CH3:16])=[N:14][C:5]=2[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 116584562-Amino-4,6-dimethoxybenzoic acid

Produkt 1

HCID 115068145,7-Dimethoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-oneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

The anthranilic acid (388 mg, 1.97 mmol) prepared in Example 2 was taken up in anhydrous methylene chloride (10 mL). Triethylamine (2.36 mmol) was added followed by addition of acetic anhydride (2.36 mmol). The reaction mixture was heated at 40° C. for 18 hours. Subsequently, the reaction mixture was poured into water and extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 5,7-dimethoxy-2-methyl-3,1-benzoxazine-4-one (51% yield).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ebffd0b0898464cab00db3f99018f95
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381730B2

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