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

HRID 75772

Reaction equation

HRID 75772 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

HCID 67353512HCID 67353512, compound

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-65db4f55613543d984c30967f7bf855e
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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