Thionyl Chloride → HCID 22646571, compound

HRID 393678Notes

Reaction equation

HRID 393678 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[NH:11][CH:10]=[CH:9][C:8]2=O)(=O)C.S(Cl)([Cl:20])=O>CN(C=O)C>[Cl:20][C:8]1[C:7]2[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([OH:4])[CH:6]=2)[N:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22646641HCID 22646641, compound

Product 1

HCID 22646571HCID 22646571, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-acetoxy-7-methoxy-1,4-dihydroquinolin-4-one (6.2 g, 28 mmol) and thionyl chloride (75 ml) containing DMF (0.5 ml) was heated at reflux for 1 hour. The volatiles were removed by evaporation. The residue was suspended in methylene chloride (5 ml) and poured slowly into a stirred solution of methanol/ammonium hydroxide. The mixture was partitioned between water and methylene chloride and dried by passing through ,phase separating paper. Removal of the solvent by evaporation gave a solid which was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-hydroxy-7-methoxyquinoline.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customThe volatiles were removed by evaporation
  4. additionpoured slowly into a stirred solution of methanol/ammonium hydroxide
  5. customThe mixture was partitioned between water and methylene chloride
  6. customdried
  7. customseparating paper
  8. customRemoval of the solvent
  9. customby evaporation
  10. customgave a solid which
  11. customwas triturated with ether
  12. filtrationcollected by filtration
  13. washwashed with ether
  14. customdried under vacuum

Sources & evidence

ORD record
ord-ab5092e73aef4f97b4cadd72ff443880
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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