Ethanol → 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester

HRID 561161Notes

Reaction equation

HRID 561161 reaction equation
C([O:8][C:9]1[C:10]([F:29])=[C:11]([F:28])[CH:12]=[C:13]2[C:18]=1[N:17]([CH:19]1[CH2:21][CH2:20]1)[CH:16]=[C:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:14]2=[O:27])C1C=CC=CC=1.CCO>C1COCC1.[Pd]>[CH:19]1([N:17]2[C:18]3[C:13](=[CH:12][C:11]([F:28])=[C:10]([F:29])[C:9]=3[OH:8])[C:14](=[O:27])[C:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16]2)[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 702EthanolHCID 59003013HCID 59003013, compound

Product 1

HCID 577419351-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterYield 47.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 8-(benzyloxy)-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (3.00 g, 7.51 mmol) in THF (60 mL)-EtOH (10 mL) was hydrogenated under atmospheric pressure over 10% Pd/C (300 mg) at room temperature for 2 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. The crude product washed with Hexane and dried to yield ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxoquinoline-3-carboxylate (1.10 g, 47%) as a colorless solid.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe crude product washed with Hexane
  4. customdried

Sources & evidence

ORD record
ord-067caf195353430f9f03bbb159d4e669
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

Loading…