Benzylamine → 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester

HRID 47895Notes

Reaction equation

HRID 47895 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.C(N)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 9996650Ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

53.0 g of ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0161 mol), 15.4 ml of benzyl amine, and 37.0 g of anhydrous K2CO3 in 220 ml of acetonitrile were stirred at 100-110° C. for 1 hour. The reaction was monitored by TLC. After the solvent was evaporated, the residue was re-crystallized from ethanol to give 53.7 g of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.129 mol) in 80.0% yield, mp 133-135° C.

Workup

  1. customAfter the solvent was evaporated
  2. customthe residue was re-crystallized from ethanol

Sources & evidence

ORD record
ord-6edc285fe4854004ab27b6bfd50c009d
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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