Hydrochloric Acid → 6,7-Difluoro-1-(2-fluoroethyl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 358890Notes

Reaction equation

HRID 358890 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:15][CH3:16])[C:13]=1[F:14])[N:10]([CH2:17][CH2:18][F:19])[CH:9]=[C:8]([C:20]([O:22]CC)=[O:21])[C:7]2=[O:25].Cl>CO>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:15][CH3:16])[C:13]=1[F:14])[N:10]([CH2:17][CH2:18][F:19])[CH:9]=[C:8]([C:20]([OH:22])=[O:21])[C:7]2=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20067126Ethyl 6,7-difluoro-1-(2-fluoroethyl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 140718416,7-Difluoro-1-(2-fluoroethyl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 ml of a 4% w/v aqueous solution of sodium hydroxide were added to a solution of the whole (0.0005 mole) of the ethyl 6,7-difluoro-1-(2-fluoroethyl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (X, R9' =2-fluoroethyl) prepared as described in Step (C5) dissolved in 15 ml of methanol. The mixture was then allowed to stand at room temperature for 5 hours, after which it was acidified by adding concentrated hydrochloric acid to precipitate crystals. These crystals were collected by filtration to give 0.11 g of 6,7-difluoro-1-(2-fluoroethyl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IIa, R9' =2-fluoroethyl) as a colorless powder.

Workup

  1. custom' =2-fluoroethyl) prepared
  2. customto precipitate crystals
  3. filtrationThese crystals were collected by filtration

Sources & evidence

ORD record
ord-6f592ba08dda49e88646679453d8e506
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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