Acetic Acid → HCID 4914114, compound

HRID 2291286Notes

Reaction equation

HRID 2291286 reaction equation
C([NH:8][C:9]1[C:18]([F:19])=[C:17]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[C:16]([F:27])=[C:15]2[C:10]=1[C:11](=[O:34])[C:12]([C:31]([OH:33])=[O:32])=[CH:13][N:14]2[CH:28]1[CH2:30][CH2:29]1)C1C=CC=CC=1.C(O)(=O)C>[C].[Pd].C(O)C>[NH2:8][C:9]1[C:18]([F:19])=[C:17]([N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[C:16]([F:27])=[C:15]2[C:10]=1[C:11](=[O:34])[C:12]([C:31]([OH:33])=[O:32])=[CH:13][N:14]2[CH:28]1[CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 146641725-Benzylamino-1-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 4914114HCID 4914114, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-benzylamino-1-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (700 mg), 5% palladium-carbon (0.2 g), acetic acid (10 ml), and ethanol (15 ml) was stirred at room temperature for 30 minutes under a hydrogen stream. The catalyst was filtered off and the filtrate was evaporated under reduced pressure. After addition of water to the residue, the mixture was adjusted to pH 8 with aqueous ammonia. The resulting crystals were filtered to give 5-amino-1-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (510 mg), m.p. 254°-255° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. additionAfter addition of water to the residue
  4. filtrationThe resulting crystals were filtered

Sources & evidence

ORD record
ord-0b78857c83e54f38971dac3414b8c17f
Source dataset
uspto-grants-1989_01
Patent number
US04795751

Reaction notes

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