Water → HCID 14423853, compound

HRID 2247919Notes

Reaction equation

HRID 2247919 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([F:18])=[C:12]([F:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].Br[CH2:20][CH2:21][F:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([F:18])=[C:12]([F:17])[CH:13]=2)[N:8]([CH2:20][CH2:21][F:22])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 751784Ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-xynoline carbonate

Product 1

HCID 14423853HCID 14423853, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester (10.0 g, 39.5 mmol), 1-bromo-2-fluoroethane (25.1 g, 197.5 mmol) and potassium carbonate (10.9 g, 79 mmol) were combined in dimethylformamide (200 ml) and heated to 90° for 20 hours. The reaction mixture was poured into cold water (1.5 l), and the copious precipitate was filtered. The precipitate was washed with cold water and recrystallized from ethyl acetate to provide the title product as light brown needles, m.p. 178°-180° (8.22 g, 27.5 mmol, 70% yield).

Workup

  1. temperatureheated to 90° for 20 hours
  2. filtrationthe copious precipitate was filtered
  3. washThe precipitate was washed with cold water
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ecd9ed4af9a84432ac82f4a46d2336e4
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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