Potassium Carbonate → HCID 14576599, compound

HRID 1607299Notes

Reaction equation

HRID 1607299 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:26])=[C:11]([F:25])[CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]2[OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+:33](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O>[NH2:33][N:17]1[C:18]2[C:13](=[CH:12][C:11]([F:25])=[C:10]([F:26])[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14](=[O:24])[C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 178469672HCID 178469672, compound

Product 1

HCID 14576599HCID 14576599, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After a mixture of ethyl 8-benzyloxy-6,7-difluoro-4-hydroxy-3-quinolinecarboxylate (410 mg) and anhydrous potassium carbonate (315 mg) in dry dimethylformamide (10 ml) was stirred at room temperature for 3 hours, O-(2,4-dinitrophenyl)hydroxylamine (260 mg) was added. The mixture was stirred at room temperature for further 6.5 hours. After removal of the solvent under reduced pressure, water (12 ml) was added to the residue, and the mixture was stirred at room temperature for 3 hours. The precipitate was collected by filtration and washed with cold water and then with ether to give 405 mg of ethyl 1-amino-8-benzyloxy-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate. An analytical sample, mp 143°-144° C.; MS m/z 374 (M+), was prepared by recrystallization from methanol.

Workup

  1. stirringThe mixture was stirred at room temperature for further 6.5 hours
  2. customAfter removal of the solvent under reduced pressure, water (12 ml)
  3. additionwas added to the residue
  4. stirringthe mixture was stirred at room temperature for 3 hours
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with cold water

Sources & evidence

ORD record
ord-b3781bd89a78434ead28ac96d1ee7507
Source dataset
uspto-grants-1989_09
Patent number
US04864023

Reaction notes

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