Dimethylformamide → HCID 20083103, compound

HRID 1656735Notes

Reaction equation

HRID 1656735 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]2[OH:23].C(=O)([O-])[O-].[K+].[K+].C[N:31](C)C=O.C1(C)C=C(C)C=C(C)C=1S(NO)(=O)=O>C(Cl)Cl>[NH2:31][N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([F:12])[C:10]=2[CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:5](=[O:23])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11009332O-mesitylenesulfonylhydroxylamineHCID 178469638HCID 178469638, compound

Product 1

HCID 20083103HCID 20083103, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.7 g (32.9 mmol) of ethyl 6,7-difluoro-4-hydroxy-8-acetoxymethylquinoline-3-carboxylate and 14.2 g (65.8 mmol) of anhydrous potassium carbonate were added to 130 ml of N,N-dimethylformamide, and the solution was stirred at room temperature for 4 hours. 14 g (NET 8.97 g, 49 mmol) of mesitylenesulfonylhydroxyamine was dissolved in 100 ml of methylene chloride, and after drying over sodium sulfate, while cooling on ice, this solution was dropped to the previous solution through 20 minutes. Then, the obtained solution was left overnight as it was. To this solution, 100 ml of water was added, and the solution was stirred at room temperature for 1 hour. The solution was extracted with methylene chloride, and the organic layer was washed. After drying over sodium sulfate, the solvent was removed under reduced pressure and ether was added to the crystal residue. The crystals were filtered off and washed with ether to obtain 6.4 g of the subject compound (97) in a 57% yield. The results of the analysis of this compound were as follows:

Workup

  1. dry with materialafter drying over sodium sulfate
  2. temperaturewhile cooling on ice
  3. additionthis solution was dropped to the previous solution through 20 minutes
  4. waitThen, the obtained solution was left overnight as it
  5. additionTo this solution, 100 ml of water was added
  6. stirringthe solution was stirred at room temperature for 1 hour
  7. extractionThe solution was extracted with methylene chloride
  8. washthe organic layer was washed
  9. dry with materialAfter drying over sodium sulfate
  10. customthe solvent was removed under reduced pressure and ether
  11. additionwas added to the crystal residue
  12. filtrationThe crystals were filtered off
  13. washwashed with ether

Sources & evidence

ORD record
ord-b9f271f6abfc407abe584e8ebee5db0c
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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