Thionyl Chloride → HCID 21891598, compound

HRID 720320Notes

Reaction equation

HRID 720320 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]=2[O:17][CH3:18])[N:8]=1>ClCCl>[Cl:3][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]=2[O:17][CH3:18])[N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21891575HCID 21891575, compound

Product 1

HCID 21891598HCID 21891598, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.7 mL) was added to a solution of 2-hydroxymethyl-5,6,7-trimethoxyquinoline (1.45 g) in dichloromethane (15 mL) under ice cooling, and the mixture was stirred at room temperature for 30 minutes. After concentrating the reaction mixture under reduced pressure, an aqueous solution of potassium carbonate was added to the residue to alkalify it. The thus-treated residue was extracted with diethyl ether. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure
  2. additionan aqueous solution of potassium carbonate was added to the residue
  3. extractionThe thus-treated residue was extracted with diethyl ether
  4. washThe resultant organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-e4368a7d227345d9afc744270f4b5076
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

Loading…