Hydrochloric Acid → HCID 89536562, compound

HRID 2171248Notes

Reaction equation

HRID 2171248 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:5]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[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]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68027926HCID 68027926, compound

Product 1

HCID 89536562HCID 89536562, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 5M sodium hydroxide aqueous solution (2 ml) was added to a THF/MeOH (2 ml/2 ml) solution containing methyl 5-fluoro-6-(2-methoxyethoxy)nicotinate (264 mg) obtained in the 2nd step, followed by stirring at room temperature for 1 hour. Next, 6M hydrochloric acid (2 ml) was added to the reaction solution at 5° C. or less 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-(2-methoxyethoxy)nicotinic acid (197 mg) was thus obtained.

Workup

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

Sources & evidence

ORD record
ord-31701d8acb624510b595ef3941e2f4bf
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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