HCID 23284719, compound → HCID 23284730, compound

HRID 369326Notes

Reaction equation

HRID 369326 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:25])=[C:18]([N+:22]([O-])=O)[C:19]=3[CH3:21])[C:14](=[O:26])[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:12]2)=[C:4]([CH3:32])[CH:3]=1>[Fe].C(O)(=O)C>[NH2:22][C:18]1[C:19]([CH3:21])=[C:20]2[C:15]([C:14](=[O:26])[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:12][N:11]2[C:5]2[CH:6]=[C:7]([NH2:8])[C:2]([F:1])=[CH:3][C:4]=2[CH3:32])=[CH:16][C:17]=1[F:25]

Participants

4

Reactant 1

HCID 23284719HCID 23284719, compound

Product 1

HCID 23284730HCID 23284730, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Acetic acid (10 ml) and iron powder (1.6 g) were added to ethyl 1-(4-fluoro-2-methyl-5-nitrophenyl)-6-fluoro-8-methyl-7-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.1 g), and the mixture was stirred overnight at 90° C. The catalyst in the reaction mixture was removed by filtration through Celite, and the solvent in the residue was distilled off. The resultant residue was purified by column chromatography on silica gel (chloroform:methanol 20:1) to obtain the title compound (230 mg) as a yellow amorphous substance.

Workup

  1. customThe catalyst in the reaction mixture was removed by filtration through Celite
  2. distillationthe solvent in the residue was distilled off
  3. customThe resultant residue was purified by column chromatography on silica gel (chloroform:methanol 20:1)

Sources & evidence

ORD record
ord-fcf4082e7c774c84b742e73c213a98e9
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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