Potassium Carbonate → Ethyl 1-(5-amino-6-chloropyridine-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 610198Notes

Reaction equation

HRID 610198 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]=[C:11]([C:17](=[O:28])[C:18]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([Cl:26])[C:19]=2F)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[N:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:19]3[C:18](=[CH:23][C:22]([F:24])=[C:21]([F:25])[C:20]=3[Cl:26])[C:17](=[O:28])[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10]2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178471960HCID 178471960, compound

Product 1

HCID 22121231Ethyl 1-(5-amino-6-chloropyridine-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 72.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 180 mg ethyl 3-[(5-amino-6-chloropyridin-3-yl)amino]-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate in 3 ml N,N-dimethylformamide was added 57 mg of potassium carbonate, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water, and extracted by adding ethyl acetate. The organic layer was separated and dried over magnesium sulfate, and the solvent was distilled off. The solid content was collected by filtration to obtain 125 mg of the title compound as a pale yellow powder.

Workup

  1. extractionextracted
  2. additionby adding ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off
  6. filtrationThe solid content was collected by filtration

Sources & evidence

ORD record
ord-09e7ac446b9f495c8d2eea95a948a336
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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