Thionyl Chloride → Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

HRID 393665Notes

Reaction equation

HRID 393665 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH:8]=[CH:9][NH:10]2)=[CH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15].S(Cl)([Cl:20])=O>CN(C=O)C>[Cl:20][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22646623Methyl 1,4-dihydro-7-methoxy-4-oxo-6-quinolinecarboxylate

Product 1

HCID 22646520Methyl 4-chloro-7-methoxyquinoline-6-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-methoxy-6-methoxycarbonyl-1,4-dihydroquinolin-4-one (5.4 g, 23 mmol), DMF (0.4 ml) and thionyl chloride (75 ml) was heated at reflux for 2 hours and then stirred at ambient temperature for a further 2 hours. The excess thionyl chloride was removed by evaporation and by azeotroping with toluene. The residue was suspended in methylene chloride and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried by passing through phase separating paper and the solvent was removed by evaporation. The residue was suspended in ether, collected by filtration, washed with hexane and dried to give 4-chloro-7-methoxy-6-methoxycarbonylquinoline (4.06 g, 70%) as an orange solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe excess thionyl chloride was removed by evaporation
  4. customby azeotroping with toluene
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. customThe organic layer was separated
  7. customdried
  8. customseparating paper
  9. customthe solvent was removed by evaporation
  10. filtrationcollected by filtration
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-5980cf10db914ccab7897e125208a955
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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