Water → 5-Nitro-3,4-dihydro-2H-1,4-benzoxazine

HRID 868984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 868984
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][CH2:14]Br.[OH-].[K+].O>CN(C)C=O>[N+:8]([C:7]1[C:2]2[NH:1][CH2:14][CH2:13][O:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 41154952-Amino-3-Nitrophenol

Produkt 1

HCID 150923655-Nitro-3,4-dihydro-2H-1,4-benzoxazineAusbeute 14,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

To a solution of 2-amino-3-nitrophenol (15.0 g, 97 mmol) and 1,2-dibromoethane (29.1 g, 155 mmol) in dimethylformamide (80 mL) was added KOH (10.9 g, 194 mmol) at 180° C. After stirring at 200° C. for 2 days, the mixture was poured to 150 g water. The mixture was concentrated under reduced pressure. The crude product was purified using column chromatography to give the title compound (2.50 g) as a red solid. MS (ESI): m/z 181 [M+H]+

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-54d706f37cf44ef6bb24c7d791c52aa0
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969349B2

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