Thionyl Chloride → 7-Benzyloxy-4-chloro-6-methoxyquinoline hydrochloride

HRID 393597Notes

Reaction equation

HRID 393597 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[CH:14]=[CH:15][NH:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>CN(C=O)C>[ClH:24].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 226465797-(Benzyloxy)-6-methoxyquinolin-4-ol

Product 1

HCID 226465617-Benzyloxy-4-chloro-6-methoxyquinoline hydrochlorideYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 7-benzyloxy-6-methoxy-1,4-dihydroquinolin-4-one (3.37 g, 13 mmol) in thionyl chloride (50 ml) and DMF (0.25 ml) was heated at reflux for 1 hour. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene and triturated with ether, the product collected by filtration and dried under vacuum to give 7-benzyloxy-4-chloro-6-methoxyquinoline hydrochloride (3.9 g, 89%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. customtriturated with ether
  6. filtrationthe product collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-094caedd26f4441b8cddbeec629c37ed
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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