Hydrochloric Acid → 6-Fluoro-7-(pyrrol-1-yl)-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 4559Notes

Reaction equation

HRID 4559 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH3:17])[CH:7]=[C:6]([C:18]([O:20]CC)=[O:19])[C:5]2=[O:23].C(O)C.[OH-].[Na+].Cl>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH3:17])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 13670061Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 136700626-Fluoro-7-(pyrrol-1-yl)-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 68.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.2 g of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate, 10 ml of ethanol, 15 ml of 10% sodium hydroxide solution and 10 ml of water is heated under reflux for 2 hours. 30 ml of 8M hydrochloric acid are added, the mixture is left to cool and the product is filtered off, washed with water and recrystallized from acetic acid to give 0.75 g of a solid melting at 284°-285° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. waitthe mixture is left
  4. temperatureto cool
  5. filtrationthe product is filtered off
  6. washwashed with water
  7. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-5aa3d23c953f421bba97f65963e5ba38
Source dataset
uspto-grants-1988_02
Patent number
US04727080

Reaction notes

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