Benzylamine → HCID 54229857, compound

HRID 1415951Notes

Reaction equation

HRID 1415951 reaction equation
F[C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6][N:7]2[C:15]1[CH:20]=[C:19]([NH:21][CH:22]=[O:23])[C:18]([F:24])=[CH:17][C:16]=1[F:25].[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH2:32]([NH:39][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6][N:7]2[C:15]1[CH:20]=[C:19]([NH:21][CH:22]=[O:23])[C:18]([F:24])=[CH:17][C:16]=1[F:25])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 54287403HCID 54287403, compound

Product 1

HCID 54229857HCID 54229857, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 30 ml of toluene were added 800 mg of ethyl 5,6,7,8-tetrafluoro-1-(2,4-difluoro-5-formylaminophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate, 0.21 ml of benzylamine, and 240 mg of anhydrous potassium carbonate. The solution was heated at reflux overnight. The reaction solution was allowed to cool down and concentrated in vacua. The residue was combined with chloroform and washed with water. The solution was dried over magnesium sulfate and the solvent was distilled off. Diethyl ether was added to the residue. The solid was collected by filtration and washed with diethyl ether to give 600 mg of the title compound.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux overnight
  3. temperatureto cool down
  4. concentrationconcentrated in vacua
  5. washwashed with water
  6. dry with materialThe solution was dried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. additionDiethyl ether was added to the residue
  9. filtrationThe solid was collected by filtration
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-685dbc7d591a4373a81d44cccf80646c
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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