HCID 11743730, compound → HCID 86588306, compound

HRID 1007081Notes

Reaction equation

HRID 1007081 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][C:17]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[C:18]([F:23])[CH:19]=2)[N:14]([CH2:30][CH3:31])[CH:13]=1)=[O:11])([O-:3])=[O:2].Cl.CCOC(C)=O>C(Cl)Cl.[N+]([O-])([O-])=O.[Ag+]>[N+:1]([O-:4])([OH:3])=[O:2].[N+:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][C:17]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[C:18]([F:23])[CH:19]=2)[N:14]([CH2:30][CH3:31])[CH:13]=1)=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 11743730HCID 11743730, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 86588306HCID 86588306, compoundYield 176.7%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid 4-nitrooxybutyl ester (300 mg, 0.68 mmoles) in CH2Cl2 (5 ml) was added HCl—AcOEt 1 M (0.8 ml). After stirring for 1 hour at room temperature, the solvent was evaporated under a reduced pressure. The residue was dissolved in THF (10 ml) and silver nitrate (120 mg, 0.70 mmoles) was added. The mixture was stirred for 1 hour at room temperature, the suspension was filtered and the precipitate washed with THF and dried to afford 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid 4-nitrooxybutyl ester nitrate salt (300 mg) as an amorphous solid. Yield 85%.

Workup

  1. customthe solvent was evaporated under a reduced pressure
  2. dissolutionThe residue was dissolved in THF (10 ml)
  3. stirringThe mixture was stirred for 1 hour at room temperature
  4. filtrationthe suspension was filtered
  5. washthe precipitate washed with THF
  6. customdried

Sources & evidence

ORD record
ord-3f3c9d995b3145c192564fcaa2ef489f
Source dataset
uspto-grants-2004_09
Patent number
US06794372B2

Reaction notes

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