Dimethyl Sulfoxide → HCID 59398252, compound

HRID 2193297Notes

Reaction equation

HRID 2193297 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]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=2)[C:20]([O:31][CH3:32])=[CH:19][C:18]1=[O:33]>O.C(N(CC)CC)C>[CH3:32][O:31][C:20]1[C:21]2[C:26](=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=2)[N:17]([CH2:16][CH:15]=[O:14])[C:18](=[O:33])[CH:19]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 59397984HCID 59397984, compound

Product 1

HCID 59398252HCID 59398252, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 2 mL of a dichloromethane solution containing 30 μL of oxalyl chloride, 50 μL of dimethylsulfoxide was added dropwise under nitrogen atmosphere at −60° C., and stirred for 13 min. 6 mL of a dichloromethane solution containing 0.08 g of 1-(2-hydroxyethyl)-4-methoxy-7-trifluoromethylquinolin-2(1H)-one was added dropwise at the same temperature, and stirred for 10 min. After 0.16 mL of triethylamine was added at the same temperature, it was stirred at room temperature for 1 hour, and 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 (4-methoxy-7-trifluoromethyl-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 10 min
  4. stirringwas stirred at room temperature for 1 hour
  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-4a9f0ff662804efdad6dffc2dd8d6201
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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