Nitric Acid → HCID 178434743, compound

HRID 1042980Notes

Reaction equation

HRID 1042980 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:17])=[CH:12][CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1.[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)CC>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:17])=[C:12]([N+:19]([O-:21])=[O:20])[CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178434741HCID 178434741, compound2×

Product 1

HCID 178434743HCID 178434743, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 7-(3,5-dimethyl-4-isoxazolyl)-4-quinolinol (for a preparation see Intermediate 11, 8.5 g, 35 mmol) in propanoic acid (442 ml) was added nitric acid (7 ml) at room temperature, followed by heating the reaction mixture to 125° C. for 2 h. After cooling, the mixture was filtered, washed with isopropyl ether to give the title compound as a yellow solid (7.5 g, 75%). [APCI-MS] m/z: 283 [M−H]−, Rt 2.41 min.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-dac374aadd9c472d81773b76bca16b6d
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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