1,1-Dichloroethane → Ethyl 1-(2,4-difluoro-5-nitrophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1415921Notes

Reaction equation

HRID 1415921 reaction equation
Cl[CH:2](Cl)[CH3:3].[F:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[N:16]1[C:25]2[C:20](=[CH:21][C:22]([F:27])=[C:23]([F:26])[CH:24]=2)[C:19](=[O:28])[C:18]([C:29]([OH:31])=[O:30])=[CH:17]1.C(Cl)(=O)C(Cl)=O>C(O)C>[F:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[N:16]1[C:25]2[C:20](=[CH:21][C:22]([F:27])=[C:23]([F:26])[CH:24]=2)[C:19](=[O:28])[C:18]([C:29]([O:31][CH2:2][CH3:3])=[O:30])=[CH:17]1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 65578Oxalyl chlorideHCID 158603631-(2,4-Difluoro-5-nitrophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 15860364Ethyl 1-(2,4-difluoro-5-nitrophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 40 ml of dichloroethane was added 4.2 g of 1-(2,4-difluoro-5-nitrophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. With ice cooling, 7 g of oxalyl chloride was added dropwise. After the completion of addition, the solution was stirred for 2 hours at room temperature. Ethanol (15 ml) was added dropwise to the reaction solution, which was stirred overnight at room temperature. The reaction solution was concentrated in vacua, ethanol was added to the residue, and the solid was collected by filtration and washed with diethyl ether to give 3.7 g of the title compound.

Workup

  1. additionAfter the completion of addition
  2. stirringwas stirred overnight at room temperature
  3. concentrationThe reaction solution was concentrated in vacua, ethanol
  4. additionwas added to the residue
  5. filtrationthe solid was collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-3e7f980761f04970ac223f10cc0f4db5
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

Loading…