Hydrochloric Acid → 9-Nitro-2,3-dihydro-4,1-benzoxazepin-5(1H)-one

HRID 1698538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698538
OC[CH2:3][NH:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].Cl>C1COCC1.O>[N+:15]([C:14]1[C:5]2[NH:4][CH2:3][CH2:10][O:9][C:7](=[O:8])[C:6]=2[CH:11]=[CH:12][CH:13]=1)([O-:17])=[O:16]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 11253443Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate

Produkt 1

HCID 672730729-Nitro-2,3-dihydro-4,1-benzoxazepin-5(1H)-oneAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2.00 g (8.32 mmol) of methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate in 150 mL of THF was added dropwise 6N HCl (100 mL) at 0° C. and the mixture was stirred for 30 min. The reaction mixture was refluxed for 16 h. After being cooled to room temperature, the mixture was diluted with water (150 ml), and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with aqueous sodium hydrogen sulfate and water. The organics was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 1.03 g (5.00 mmol, 60%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous sodium hydrogen sulfate and water
  5. dry with materialThe organics was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-248eea2a4158459ea010d7061f96103c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163935B2

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