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Water → Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2247921
Notes
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Reaction equation

HRID 2247921 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].CI.[C:21](=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]([CH3:21])[CH:7]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 751784Ethyl 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 14423855Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

6,7-Difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester (10.0 g, 39.5 mmol), methyl iodide (56 g, 395 mmol) and potassium carbonate (10.9 g, 79 mmol) were combined in dimethylformamide and heated to 90° for 20 hours. The reaction mixture was cooled and poured into cold water (1.5 l). The precipitate was filtered, washed with cold water and recrystallized from ethyl acetate to yield the title product as white needles, m.p. 210°-212° (6.60 g, 24.7 mmol, 63% yield).

Workup

  1. temperatureheated to 90° for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-18b7ea7aa6a24994ac5c2d7ed19090e5
Source dataset
uspto-grants-1991_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05037834

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes