Hydrochloric Acid → HCID 89666853, compound

HRID 2171244Notes

Reaction equation

HRID 2171244 reaction equation
[OH-].[K+].[F:3][C:4]1[C:5]([N:14]2[N:18]=[CH:17][CH:16]=[N:15]2)=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([O:11]C)=[O:10].Cl>C1COCC1.CO>[F:3][C:4]1[C:5]([N:14]2[N:18]=[CH:17][CH:16]=[N:15]2)=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 89666803HCID 89666803, compound

Product 1

HCID 89666853HCID 89666853, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 5M potassium hydroxide aqueous solution (2 ml) was added to a THF/MeOH (2 ml/2 ml) solution containing methyl 5-fluoro-6-(2H-1,2,3-triazol-2-yl)nicotinate (250 mg), followed by stirring at room temperature for 1 hour. 6M hydrochloric acid was added to the reaction solution so as to acidify the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and a white solid of 5-fluoro-6-(2H-1,2,3-triazol-2-yl)nicotinic acid (198 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layers were washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-4569ba53fd2f44d8b04d7e584f2bf191
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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