Nitric Acid → HCID 178526772, compound

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

Reactant 2

HCID 944Nitric Acid

HCID 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

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

Sources & evidence

ORD record: ord-ade38e657db34f9b8b3b64abca6f5575
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323200B1

Reaction notes

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