Nitric Acid → HCID 178526772, compound

HRID 430573Notes

Reaction equation

HRID 430573 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-ade38e657db34f9b8b3b64abca6f5575
Source dataset
uspto-grants-2001_11
Patent number
US06323200B1

Reaction notes

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