Hydrochloric Acid → 2-Pyridinecarboxylicacid,5-(2,2,3,3-tetrafluoropropoxy)-

HRID 1186195Notes

Reaction equation

HRID 1186195 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:18])([F:17])[CH:14]([F:16])[F:15])=[CH:7][N:6]=1)=[O:4].[OH-].[Li+].Cl>C1COCC1.O>[F:18][C:13]([F:17])([CH:14]([F:16])[F:15])[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 574758745-(2,2,3,3-Tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 574758552-Pyridinecarboxylicacid,5-(2,2,3,3-tetrafluoropropoxy)-Yield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 5-(2,2,3,3-tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester (2.6 g) in THF (20 ml) and water (15 ml) was added lithium hydoxide solution (1 M, 19.4 ml) and the reaction mixture was stirred at 22° C. for 30 min. The reaction mixture was neutralised by addition of aqueous HCl (1 N, 19.4 ml), the organic solvent was evaporated, the suspension obtained still containing water was filtered and the residue was dried to give 5-(2,2,3,3-tetrafluoro-propoxy)-pyridine-2-carboxylic acid (2.3 g) as an off-white solid.

Workup

  1. customthe organic solvent was evaporated
  2. customthe suspension obtained still containing water
  3. filtrationwas filtered
  4. customthe residue was dried

Sources & evidence

ORD record
ord-617827e90220428d9f426bcb3da4661a
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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