Acetic Acid → HCID 23284704, compound

HRID 369211Notes

Reaction equation

HRID 369211 reaction equation
C([NH:8][C:9]1[C:18]([Cl:19])=[C:17]2[C:12]([C:13](=[O:41])[C:14]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:15][N:16]2[C:20]2[CH:25]=[C:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:23]([F:34])=[CH:22][C:21]=2[F:35])=[CH:11][C:10]=1[F:42])C1C=CC=CC=1.C(O)(=O)C.[H][H]>ClCCCl.[OH-].[Pd+2].[OH-]>[NH2:8][C:9]1[C:18]([Cl:19])=[C:17]2[C:12]([C:13](=[O:41])[C:14]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:15][N:16]2[C:20]2[CH:25]=[C:24]([NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[C:23]([F:34])=[CH:22][C:21]=2[F:35])=[CH:11][C:10]=1[F:42]

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 23284708HCID 23284708, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23284704HCID 23284704, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 111,2-DichloroethaneSolvent

Procedure

Ethyl 7-benzylamino-1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (3.2 g) was dissolved in 1,2-dichloroethane (40 ml). An acetic acid suspension (10 ml) of 20% palladium hydroxide (300 mg) was added to this solution, and the mixture was stirred overnight at 60° C. in a hydrogen atmosphere. An acetic acid suspension (4 ml) of 20% palladium hydroxide (100 mg) was additionally added, and the resultant mixture was stirred overnight at the same temperature. After the reaction mixture was cooled back to room temperature, palladium hydroxide was removed by filtration. After the solvent was distilled off under reduced pressure, diisopropyl ether was added to the residue, and solids were collected by filtration to obtain the title compound (2.5 g) as an amorphous substance.

Workup

  1. custompalladium hydroxide was removed by filtration
  2. distillationAfter the solvent was distilled off under reduced pressure, diisopropyl ether
  3. additionwas added to the residue, and solids
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-924d5c183056484ca0b6e5963cbc8130
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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