Nitric Acid → HCID 178526762, compound

HRID 2380395Notes

Reaction equation

HRID 2380395 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, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
125 °C

Procedure

4-Hydroxyquinoline (26.2 g, 0.18 mol) was added to propionic acid (250 mL) and the solution was heated to about 125° C. Nitric acid (16.0 mL of a 70 percent aqueous solution, 0.36 mol) was added dropwise with stirring. When the addition was complete, the mixture was stirred at about 125° C. for 10 minutes, then allowed to cool to room temperature. The mixture was diluted with ethanol. The precipitated solid was filtered, washed sequentially with ethanol, water, and ethanol, and dried to afford 3-nitro-4-hydroxyquinoline (27.7 g, 86%) as a light yellow powder.

Workup

  1. additionWhen the addition
  2. stirringthe mixture was stirred at about 125° C. for 10 minutes
  3. temperatureto cool to room temperature
  4. filtrationThe precipitated solid was filtered
  5. washwashed sequentially with ethanol, water, and ethanol
  6. customdried

Sources & evidence

ORD record
ord-33dcb356def147f1b696fa52cb6cb549
Source dataset
uspto-grants-1994_11
Patent number
US05367076

Reaction notes

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