Nitric Acid → HCID 178526772, compound

HRID 1872647Notes

Reaction equation

HRID 1872647 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178516426HCID 178516426, compound

Product 1

HCID 178526772HCID 178526772, compound

Procedure

7-Chloro-4-hydroxyquinoline (35 g, 0.195 mol; available from Aldrich, Milwaukee, Wis.) and nitric acid (350 mL of 70%) were combined and heated at reflux for 75 minutes. The reaction mixture was poured over ice while still hot. The resulting bright yellow precipitate was isolated by filtration and then washed 3 times with boiling ethyl acetate to provide 17.3 g of 7-chloro-3-nitro-4-hydroxyquinoline as a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 75 minutes
  3. additionThe reaction mixture was poured over ice while still hot
  4. customThe resulting bright yellow precipitate was isolated by filtration
  5. washwashed 3 times with boiling ethyl acetate

Sources & evidence

ORD record
ord-bcbe5ce4feb649d19936abd07620fa88
Source dataset
uspto-grants-2000_08
Patent number
US06110929

Reaction notes

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