Sulfuric Acid → HCID 178418458, compound

HRID 2961Notes

Reaction equation

HRID 2961 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:18])=[C:5]([C:13]([O:15]CC)=[O:14])[CH:6]=[N:7]2.S(=O)(=O)(O)O>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:18])=[C:5]([C:13]([OH:15])=[O:14])[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:18])=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 178418446HCID 178418446, compound2×

Product 2

HCID 178418458HCID 178418458, compoundHCID 178418483HCID 178418483, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

5,7-Dichloro-3-ethoxycarbonyl-4-hydroxyquinoline (114.4 g; 0.4 mole) and 343.2 g of 70% sulfuric acid were charged in a 1,000 ml four-necked flask equipped with stirrer, thermometer and distilling tube and the mixture was heated at 150° C. with stirring. Reaction was continued by heating up to 165° C. during three hours together with evaporation of the by-produced ethanol outside the reaction system. The reaction product was analyzed by liquid chromatography whereupon and it was found that the starting 5,7-dichloro-3-ethoxycarbonyl-4-hydroxy-quinoline disappeared and that 5,7-dichloro-3-carboxy-4-hydroxyquinoline in 22% yield and 5,7-dichloro-4-hydroxyquinoline in 78% yield were produced.

Workup

  1. customequipped with stirrer
  2. distillationthermometer and distilling tube
  3. customReaction

Sources & evidence

ORD record
ord-57265bf9bb574995a79f159928fe6a0d
Source dataset
uspto-grants-1998_03
Patent number
US05731440

Reaction notes

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