Nitric Acid → HCID 178526772, compound

HRID 1168830Notes

Reaction equation

HRID 1168830 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-9ed531fa392749c4914f4502fc734b13
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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