Thionyl Chloride → 4-Chloro-6,7-dimethoxyquinoline hydrochloride

HRID 393587

Reaction equation

HRID 393587 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=O.S(Cl)([Cl:18])=O>CN(C=O)C>[ClH:18].[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 4596116,7-Dimethoxy-4-hydroxyquinoline

Product 1

HCID 226465434-Chloro-6,7-dimethoxyquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6,7-dimethoxy-1,4-dihydroquinolin-4-one (3 g, 14 mmol), (J. Chem. Soc. 1940, 1209), in thionyl chloride (60 ml) and DMF (0.3 ml) was heated at reflux for 3 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene and washed with ether to give 4-chloro-6,7-dimethoxyquinoline hydrochloride.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. washwashed with ether

Sources & evidence

ORD record
ord-d6a9307ea24f421bade5e071b6ab5a54
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Linked notes

Loading…