Dimethyl Sulfoxide → HCID 59398420, compound

HRID 2193296Notes

Reaction equation

HRID 2193296 reaction equation
ClCCl.C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:14][CH2:15][CH2:16][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[O:27][CH3:28])[CH:20]=[CH:19][C:18]1=[O:29]>O.C(N(CC)CC)C>[CH3:28][O:27][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:26]=1[N:17]([CH2:16][CH:15]=[O:14])[C:18](=[O:29])[CH:19]=[CH:20]2

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 59397980HCID 59397980, compound

Product 1

HCID 59398420HCID 59398420, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 4 mL of a dichloromethane solution containing 0.07 mL of oxalyl chloride, 0.11 mL of dimethylsulfoxide was added dropwise under nitrogen atmosphere at −60° C., and stirred for 10 min. 10 mL of a dichloromethane solution containing 0.14 g of 1-(2-hydroxyethyl)-8-methoxyquinolin-2(1H)-one was added dropwise at the same temperature, and stirred for 12 min. After 0.36 mL of triethylamine was added at the same temperature, it was stirred at room temperature for 1.5 hours, and 20 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 (8-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde as a pale yellow solid.

Workup

  1. additionwas added dropwise under nitrogen atmosphere at −60° C.
  2. additionwas added dropwise at the same temperature
  3. stirringstirred for 12 min
  4. stirringwas stirred at room temperature 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-2990706934354d3a80560846d1efab57
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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