Ethyl Acetate → 2-butyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234902
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=1[OH:12].C(OCC)(=O)C.C(=O)([O-])O.[Na+].Br[CH:25]([CH2:29][CH2:30][CH2:31][CH3:32])[C:26](Br)=[O:27]>O>[CH2:29]([CH:25]1[C:26](=[O:27])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=2[O:12]1)[CH2:30][CH2:31][CH3:32]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 30169232-Bromohexanoyl bromideHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Produkt 1

HCID 105394732-butyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazineAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-methoxycarbonylphenol [Tetrahedron, 4.6 (15), 5177-5186 (1990)] (8.0 g) in a mixed solvent of ethyl acetate (200 ml) and water (200 ml) were added sodium hydrogen carbonate (11.18 g) and 2-bromohexanoyl bromide (12.73 g) and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in dimethylformamide (300 ml), to the solution was added potassium carbonate (6.0 g) and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The solvent was distilled off under reduced pressure and the resulting crystals were recrystallized from ether to give 2-butyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (10.3 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe resulting residue was dissolved in dimethylformamide (300 ml), to the solution
  4. additionwas added potassium carbonate (6.0 g)
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. additionWater was added to the reaction solution and extraction with ethyl acetate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting crystals were recrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-5e0192d32cc24e3e8c8abb93cd56ba12
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597820

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