Dimethyl Sulfoxide → HCID 59398353, compound

HRID 2193276Notes

Reaction equation

HRID 2193276 reaction equation
ClCCl.C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:14][C:15]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19](=[O:30])[N:20]2[CH2:27][CH2:28][OH:29]>O.C(N(CC)CC)C>[Cl:14][C:15]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19](=[O:30])[N:20]2[CH2:27][CH:28]=[O:29]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 59398118HCID 59398118, compound

Product 1

HCID 59398353HCID 59398353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 1.2 mL of a dichloromethane solution containing 21 μL of oxalyl chloride, 26 μL of dimethylsulfoxide was added dropwise under nitrogen atmosphere at −78° C., and stirred for 15 min. 1 mL of a dichloromethane solution containing 31 mg of 5-chloro-1-(2-hydroxyethyl)-8-methoxyquinolin-2(1H)-one was added dropwise at the same temperature, and stirred for 30 min. 84 μL of triethylamine was added at the same temperature, the mixture was stirred for 1.5 hours while slowly raising the reaction mixture to room temperature, and 0.5 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give (5-chloro-8-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde as a yellow solid.

Workup

  1. additionwas added dropwise under nitrogen atmosphere at −78° C.
  2. additionwas added dropwise at the same temperature
  3. stirringstirred for 30 min
  4. stirringthe mixture was stirred for 1.5 hours
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f47e8d3e992e426fa020ac1dd7ee8243
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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