2-Aminophenol → Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

HRID 253108

Reaktionsgleichung

Reaktionsgleichung von HRID 253108
Br[CH:2]([CH2:8]Br)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:17]1[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:8][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2

Komponenten

5

Edukt 3

HCID 58012-AminophenolHCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionate

Produkt 1

HCID 31090Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2,3-dibromopropionate (8.05 g, 31.0 mmol, Aldrich) in acetone (35 mL) was added o-aminophenol (3.38 g. 31.0 mmol) and potassium carbonate (5.1 g, 36.9 mmol). The reaction mixture was stirred at reflux under a water condenser for 18 h. Upon cooling to room temperature, the reaction was concentrated in vacuo, and the residue was taken up in water (50 mL) and the product was extracted using EtOAc (3×75 mL). The organic fractions were combined, washed with saturated brine (15 mL), dried over sodium sulfate, and concentrated. Purification of the product by flash column chromatography (30% EtOAc/hexane) afforded the title compound as a yellow oil. MS m/z: 208 (M+1).

Aufarbeitung

  1. temperatureat reflux under a water condenser for 18 h
  2. concentrationthe reaction was concentrated in vacuo
  3. extractionthe product was extracted
  4. washwashed with saturated brine (15 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the product by flash column chromatography (30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f679ff5520a7421c8a797bbebdd28209
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872009B2

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