Potassium Hydroxide → 5-(2-Fluorophenoxy)-2-pyrazinecarboxylic acid

HRID 340092Notes

Reaction equation

HRID 340092 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:7][N:6]=1)=[O:4].[OH-].[K+]>C(O)C>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][C:8]1[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 71238257HCID 71238257, compound

Product 1

HCID 463182515-(2-Fluorophenoxy)-2-pyrazinecarboxylic acidYield 51.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Fluoro-phenoxy)-pyrazine-2-carboxylic acid methyl ester (Preparation 44, 57.9 g, 233 mmol) was added to a solution of KOH (15 g, 267 mmol) in 78% ethanol (330 mL). The solution was stirred at room temperature for 18 hours, and the formed precipitate was collected by filtration. The resulting solid was dissolved in water (200 mL), and the solution was acidified with aqueous hydrochloric acid. The formed precipitate was collected by filtration, dried and recrystallised from 41% ethanol (265 mL) to give the title compound (28.3 g, 120.8 mmol) in 51.8% yield.

Workup

  1. filtrationthe formed precipitate was collected by filtration
  2. dissolutionThe resulting solid was dissolved in water (200 mL)
  3. filtrationThe formed precipitate was collected by filtration
  4. customdried
  5. customrecrystallised from 41% ethanol (265 mL)

Sources & evidence

ORD record
ord-318af253e5ac47f987cfe7f46a9f65f9
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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