Potassium Carbonate → Ethyl 5,7-dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 36712Notes

Reaction equation

HRID 36712 reaction equation
[Cl:1][C:2]1[C:20]([F:21])=[C:19]([Cl:22])[CH:18]=[C:17](F)[C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH:14]1[CH2:16][CH2:15]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:20]([F:21])=[C:19]([Cl:22])[CH:18]=[C:17]2[C:3]=1[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][N:13]2[CH:14]1[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178471887HCID 178471887, compound

Product 1

HCID 15070039Ethyl 5,7-dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6 g of ethyl 2-(2,4-dichloro-3,6-difluorobenzoyl)-3-cyclopropylamino-acrylate are heated in 100 ml of dimethylformamide at 150° C. with 2.75 g of potassium carbonate for 2.5 hours. The mixture is poured into 600 ml of ice-water and the precipitate is filtered off with suction, washed with water and dried. 5.2 g of ethyl 5,7-dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate of melting point 227°-229° C. are obtained.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-601fd3f6af404c4ba1922c4afe7f822e
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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