Sodium Bicarbonate → 2H-1,2-Benzoxazin-3(4H)-one

HRID 375522

Reaktionsgleichung

Reaktionsgleichung von HRID 375522
[O:1]=[C:2]1[NH:7]C2C=C([N+]([O-])=O)C=CC=2O[CH2:3]1.N[C:16]1[CH:21]=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][C:17]=1[OH:25].C(=O)(O)[O-].[Na+]>C(C(C)=O)C(C)C>[O:25]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:3][C:2](=[O:1])[NH:7]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-oneHCID 36133892-Amino-4-Nitrophenol

Produkt 1

HCID 199374482H-1,2-Benzoxazin-3(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

3-Oxo-6-nitro-3,4-dihydro-2H-1,4-benzoxazine. A solution of 2-amino-4-nitrophenol (8.80 g), in methyl isobutyl ketone (30 mL) was treated with sodium bicarbonate (11.5 g) and distilled water (35 mL). The mixture was cooled to 5° C. under a nitrogen atmosphere, treated dropwise with chloroacetyl chloride (5.0 mL) and then heated to reflux for 18 hours. A brown solid was collected from the cooled mixture by filtration. The solid was dried under vacuum at 50° C. for 24 hours yielding benzoxazinone (10.5 g) as a brown solid; mp 235°-236° C.; MS: m/z=195(M+1); NMR: 4.76 (s,2), 7.14 (d,1), 7.74 (d,1), 7.82 (dd,1), 11.07 (broad s,1).

Aufarbeitung

  1. distillationdistilled water (35 mL)
  2. additiontreated dropwise with chloroacetyl chloride (5.0 mL)
  3. temperatureheated
  4. temperatureto reflux for 18 hours
  5. filtrationA brown solid was collected from the cooled mixture by filtration
  6. customThe solid was dried under vacuum at 50° C. for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-d458ffb65c6f431db06977d623c64fbf
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486515

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