Thionyl Chloride → 4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

HRID 393606Notes

Reaction equation

HRID 393606 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[NH:9][CH:8]=[CH:7][C:6]2=O.S(Cl)([Cl:21])=O>CN(C=O)C>[ClH:21].[Cl:21][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 106343396-methoxy-7-(2-methoxyethoxy)quinolin-4(1H)-one

Product 1

HCID 226466534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A solution of 6-methoxy-7-(2-methoxyethoxy)-1,4-dihydroquinolin-4-one (500 mg, 2 mmol) in thionyl chloride (10 ml) and DMF (3 drops) was heated at reflux for 1 hour. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene and then triturated with ether. The solid was collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (590 mg, 95%).

Workup

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

Sources & evidence

ORD record
ord-dc37d14060ed4ef9afd90e957e3ef0ae
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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