Potassium Carbonate → HCID 20067135, compound

HRID 358893Notes

Reaction equation

HRID 358893 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([O:19][CH3:20])[C:17]=1[F:18])[N:14]=[CH:13][C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:11]2[OH:26].[N+:27](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O>[NH2:27][N:14]1[C:15]2[C:10](=[CH:9][C:8]([F:7])=[C:17]([F:18])[C:16]=2[O:19][CH3:20])[C:11](=[O:26])[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 178469677HCID 178469677, compound

Product 1

HCID 20067135HCID 20067135, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.10 g (0.008 mole) of potassium carbonate was added to a solution of 1.13 g (0.004 mole) of ethyl 6,7-difluoro-4-hydroxy-8-methoxyquinoline-3-carboxylate (IX) [prepared as described in Preparation 14 (B3)] in 20 ml of dimethylformamide and the mixture was stirred at room temperature for 3 hours. 0.81 g (0.0041 mole) of O-(2,4-dinitrophenyl)hydroxylamine was then added, and the mixture was stirred at room temperature for 6 hours. At the end of this time, the solvent was distilled from the reaction mixture under reduced pressure. The residue was washed, in turn, with water and with ethanol. The solid produced was extracted with chloroform, and the solvent was stripped from the extract, to give 0.62 g of ethyl 1-amino-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (XV) as an ocherous powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. distillationAt the end of this time, the solvent was distilled from the reaction mixture under reduced pressure
  3. washThe residue was washed, in turn, with water and with ethanol
  4. customThe solid produced
  5. extractionwas extracted with chloroform

Sources & evidence

ORD record
ord-5106c42e0d114d01b1f5421714e45145
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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