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

HRID 249290Notes

Reaction equation

HRID 249290 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>[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]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 751784Ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-xynoline carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 dimethylsformamide 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-bbb5d5d8d0c34b51b9058e30955b6ca7
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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