Nitric Acid → HCID 178526762, compound

HRID 2090227Notes

Reaction equation

HRID 2090227 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(O)(=O)CC.[N+:17]([O-])([OH:19])=[O:18]>C(O)C>[N+:17]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1032Propionic AcidHCID 178516385quinolin-4-ol

Product 1

HCID 178526762HCID 178526762, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
125 °C

Procedure

4-Hydroxyquinoline (22.2 g) and propionic acid (200 mL) were combined and heated to 125° C. Nitric acid (21.5 mL) was added dropwise over 1.5 h. The reaction mixture was stirred at reflux temperature for a further 15 min and cooled to rt. The mixture was diluted with ethanol and the solid was collected by vacuum filtration. The solid was washed with ethanol, water then ethanol. The residue was refluxed in ethanol and the hot mixture was filtered and dried to give the subtitle compound. Yield: 22 g

Workup

  1. temperatureat reflux temperature for a further 15 min
  2. temperaturecooled to rt
  3. filtrationthe solid was collected by vacuum filtration
  4. washThe solid was washed with ethanol, water
  5. temperatureThe residue was refluxed in ethanol
  6. filtrationthe hot mixture was filtered
  7. customdried

Sources & evidence

ORD record
ord-18802cd2b8d64eedb726571a3d0fd96b
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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