Hydrochloric Acid → 6-Fluoroquinoline-3-carboxylic acid

HRID 1944551Notes

Reaction equation

HRID 1944551 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([F:18])=[CH:13][CH:12]=2)=[O:7])C.Cl>CO>[F:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:17]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53403223Ethyl 6-fluoroquinoline-3-carboxylate

Product 1

HCID 170396166-Fluoroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3 N aqueous sodium hydroxide (5 mL, 15 mmol) was added to a solution of 6-fluoro-quinoline-3-carboxylic acid ethyl ester (2.2 g, 10 mmol) in methanol (50 mL). A heavy precipitate developed, and the mixture was diluted with an additional 50 mL of methanol to facilitate stirring. The mixture was stirred for 3 hours, then neutralized with of 1N hydrochloric acid (15 mL). The methanol was evaporated in vacuo, and the slurry diluted with water. The product was collected by filtration and washed with water, to give the product, 1.76 g (92%) as a colorless solid. MS: m/z 192.1 (MH+).

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. customThe methanol was evaporated in vacuo
  3. additionthe slurry diluted with water
  4. filtrationThe product was collected by filtration
  5. washwashed with water
  6. customto give the product, 1.76 g (92%) as a colorless solid

Sources & evidence

ORD record
ord-67113020b3db4e208e2b0cc4567d8035
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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