Sulfuric Acid → HCID 178418458, compound

HRID 2960Notes

Reaction equation

HRID 2960 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:15])=[C:5]([C:13]#[N:14])[CH:6]=[N:7]2.S(=O)(=O)(O)O>>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:15])=[CH:5][CH:6]=[N:7]2.[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:15])=[C:5]([C:13]#[N:14])[CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178418487HCID 178418487, compound

Product 2

HCID 178418458HCID 178418458, compoundHCID 178418487HCID 178418487, compound

Procedure

5,7-Dichloro-3-cyano-4-hydroxyquinoline (7.0 g; 0.0293 mole) and 104 g of 62.5% sulfuric acid were charged in a 300 ml four-necked flask equipped with stirrer, thermometer and reflux condenser, and the mixture was heated up to a boiling point (144°-146° C.) during one hour and subjected to a reaction at the same temperature for 15 hours. When the reaction product was analyzed by liquid chromatography, 5,7-dichloro-4-hydroxyquinoline was produced in 99% yield (where the starting 5,7-dichloro-3-cyano-4-hydroxyquinoline disappeared while an intermediate, 5,7-dichloro-3-carboxy-4-hydroxyquinoline, was produced in not more than 0.2% yield).

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and reflux condenser
  3. temperaturethe mixture was heated up to a boiling point (144°-146° C.) during one hour
  4. customsubjected to a reaction at the same temperature for 15 hours

Sources & evidence

ORD record
ord-ece997c552924fb094fb0d886a9ac725
Source dataset
uspto-grants-1998_03
Patent number
US05731440

Reaction notes

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