Hydrochloric Acid → HCID 12150700, compound

HRID 1805102Notes

Reaction equation

HRID 1805102 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14]CC)=[O:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:18][CH3:19].[OH-].[Na+].Cl>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([OH:14])=[O:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:18][CH3:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12150699ETHYL 7-FLUORO-4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLATE

Product 1

HCID 12150700HCID 12150700, compoundYield 14%

Procedure

Ethyl 7-fluoro-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (409 mg, 1.54 mmol) was suspended in a solution of NaOH (3.55 mL of 4% w/v, 3.55 mmol) and the reaction was stirred under reflux for 2 h. After cooling, the reaction mixture was acidified with conc. HCl. The resulting precipitated was collected via filtration, washed with water and dried to yield 7-fluoro-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (50 mg, 14%). LC/MS: m/z 238.3 (M+H)+ at 0.95 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureunder reflux for 2 h
  2. temperatureAfter cooling
  3. customThe resulting precipitated
  4. filtrationwas collected via filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7adc5b5985994433a6f4f227e625033b
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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