ethyl 2-(4-formyl-2-nitrophenoxy)acetate → 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

HRID 1435849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435849
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:8]=1[N+:15]([O-])=O)C>C(O)(=O)C.[Fe]>[O:3]=[C:4]1[NH:15][C:8]2[CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5]1

Komponenten

4

Edukt 1

HCID 5305379ethyl 2-(4-formyl-2-nitrophenoxy)acetate

Produkt 1

HCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehydeAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(4-Formyl-2-nitrophenoxy)acetic acid ethyl ester (1.9 g) in acetic acid (40 mL) was treated with iron powder (4.2 g) and the mixture was stirred at 60° C. for 0.75 hours, filtered and evaporated to dryness. It was partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic fraction was chromatographed on silica gel (ethyl acetate) to give a white solid (0.88 g). MS (−ve ion electrospray) m/e 176 (M−H)−.

Aufarbeitung

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customIt was partitioned between aqueous sodium bicarbonate and ethyl acetate
  4. customThe organic fraction was chromatographed on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bd2c2043dadd4b0bbe53d2c49219a2e9
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618959B2

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