HCID 13146122, compound → HCID 13146123, compound

HRID 2296375Notes

Reaction equation

HRID 2296375 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:30])=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)[C:11]=2[F:13])[C:6](=[O:31])[C:5]([C:32]([OH:34])=[O:33])=[CH:4]1)[CH3:2]>[Pd].C(O)(=O)C>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:17]2[CH2:18][CH2:19][N:14]([C:10]3[C:11]([F:13])=[C:12]4[C:7]([C:6](=[O:31])[C:5]([C:32]([OH:34])=[O:33])=[CH:4][N:3]4[CH2:1][CH3:2])=[CH:8][C:9]=3[F:30])[CH2:15][CH2:16]2)=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 13146122HCID 13146122, compound

Product 1

HCID 13146123HCID 13146123, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-ethyl-6,8-difluoro-1,4-dihydro-7-[4-(p-nitrobenzyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid (6.0 g), acetic acid (150 ml), and 5% palladium on charcoal (1.0 g) was hydrogenated. The slurry was filtered and the filtrate concentrated to dryness. The residue was treated with water, neutralized with aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was dried and evaporated. The residue was chromatographed on silica gel. Elution with a mixture of chloroform and ethanol (20:1) and recrystallization from a mixture of chloroform and ethanol gave 7-[4-(p-aminobenzyl)-1-piperazinyl]-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. filtrationThe slurry was filtered
  2. concentrationthe filtrate concentrated to dryness
  3. additionThe residue was treated with water
  4. extractionextracted with dichloromethane
  5. customThe organic layer was dried
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washElution
  9. additionwith a mixture of chloroform and ethanol (20:1) and recrystallization
  10. additionfrom a mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-b854a8968e544a2f9bc1316fe77be1e6
Source dataset
uspto-grants-1984_01
Patent number
US04429127

Reaction notes

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