Thionyl Chloride → 4-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochloride

HRID 393611Notes

Reaction equation

HRID 393611 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][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[NH:9][CH:8]=[CH:7][C:6]2=O.S(Cl)([Cl:26])=O>CN(C=O)C>[ClH:26].[Cl:26][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 226466086-Methoxy-7-(3-morpholinopropoxy)quinolin-4-ol

Product 1

HCID 226466224-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A solution of 6-methoxy-7-(3-morpholinopropoxy)-1,4-dihydroquinolin-4-one (200 mg, 0.63 mmol) in thionyl chloride (10 ml) containing DMF (3 drops) was heated at reflux for 1 hour. After removal of the volatiles by evaporation, the residue was azeotroped with toluene, triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline hydrochloride (240 mg, 93%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customAfter removal of the volatiles
  4. customby evaporation
  5. customthe residue was azeotroped with toluene
  6. customtriturated with ether
  7. filtrationcollected by filtration
  8. washwashed with ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-783099a07090462d8253ee1010646d8b
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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