Hydrochloric Acid → 4-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-3-((methyloxy)carbonyl)benzoic acid

HRID 1662537Notes

Reaction equation

HRID 1662537 reaction equation
[F:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:11]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[OH-].[K+].Cl>C1COCC1.CO>[F:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:11]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57706068Dimethyl 4-(5-fluoro-2-(methyloxy)-4-pyridinyl)-1,3-benzenedicarboxylate

Product 1

HCID 574675964-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-3-((methyloxy)carbonyl)benzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 83.21A (0.860 g, 2.7 mmol) in THF (7.00 mL) and MeOH (7.00 mL) at 0° C. was added potassium hydroxide (1.5 mL, 3.0 mmol) slowly to maintain the temperature below 6° C. The reaction mixture was allowed to warm to room temperature and stirred for 17 hours. After which, the reaction was acidified with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure to yield 83.21B as a colorless solid (0.82 g, 100% yield).

Workup

  1. temperatureto maintain the temperature below 6° C
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0811189dcd3b4d11bbcada8cf4e47215
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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