Potassium Carbonate → Ethyl 6-nitro-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

HRID 1448469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448469
Br[CH:2]([CH2:8]Br)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([NH2:26])[CH:20]=1)([O-:18])=[O:17]>CC(C)=O>[N+:16]([C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:8][NH:26][C:21]=2[CH:20]=1)([O-:18])=[O:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionateHCID 36133892-Amino-4-Nitrophenol

Produkt 1

HCID 20379906Ethyl 6-nitro-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

29.2 g of ethyl 2,3-dibromopropionate was added dropwise to a refluxing mixture of 19 g of anhydrous potassium carbonate, 70.9 g of 4-nitro-2-aminophenol and 500 ml of dry acetone. This procedure was repeated thrice. The reaction mixture was refluxed for 17 hours, then filtered. The solvent was evaporated from the filtrate under reduced pressure. The residue was washed with dilute sodium hydroxide solution, extracted with ether, then with methylene chloride. The solvent was evaporated separately from each extract. Thin layer chromatographic analysis indicated that the produce from each of the extracts was the same. The products was combined and recrystallized from ether to give 4, as a solid, m.p.: 88°-90° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 17 hours
  2. filtrationfiltered
  3. customThe solvent was evaporated from the filtrate under reduced pressure
  4. washThe residue was washed with dilute sodium hydroxide solution
  5. extractionextracted with ether
  6. customThe solvent was evaporated separately from each extract
  7. customproduce from each of the extracts
  8. customrecrystallized from ether
  9. customto give 4

Quellen und Nachweise

ORD-Eintrag
ord-b80a57ffdb0d48b480d5b1fd6211d4a3
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04180572

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