Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate → HCID 67353512, Verbindung

HRID 75772

Reaktionsgleichung

Reaktionsgleichung von HRID 75772
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5])[CH3:2].C(OC(C1ON=C(C2C=CC(N)=CC=2)C=1)=O)C>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Komponenten

3

Edukt 2

HCID 53407704Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylateHCID 673532643-(4-Nitro-phenyl)-5-phenyl-isoxazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 67353512HCID 67353512, Verbindung

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The title compound was prepared using 3-(4-nitro-phenyl)-5-phenyl-isoxazole-4-carboxylic acid ethyl ester by the same procedure as described for the preparation of 3-(4-amino-phenyl)-isoxazol-5-carboxylic acid ethyl ester in Example 1. The reaction mixture was refluxed for 16 hours instead of heating at 80° C. for 3 hours. The crude product was purified by flash chromatography over silica gel with 10% EtOAc in chloroform to give the title compound in 74% yield. IR (KBr): 3374, 1712 (br), 1628, 1610, 1439; 1H NMR (DMSO-d6) δ: 1.15 (t, 3H), 4.20 (q, 2H), 5.57 (s, 2H), 6.63 (d, 2H), 7.34 (d, 2H), 7.53-7.62 (m, 3H), 7.75-7.89 (m, 2H); Mass (ES+), 309 (M++1).

Aufarbeitung

  1. customThe title compound was prepared
  2. temperatureThe reaction mixture was refluxed for 16 hours instead
  3. customThe crude product was purified by flash chromatography over silica gel with 10% EtOAc in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-65db4f55613543d984c30967f7bf855e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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