Hydrochloric Acid → 6-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

HRID 1528364Notes

Reaction equation

HRID 1528364 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]=1)=[O:4].[OH-].[Li+].Cl>O1CCCC1.O>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=2[O:11][CH2:12][C:13]([F:16])([F:14])[F:15])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 666785906-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 666784836-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.0 g 6-(4-chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester in 30 mL tetrahydrofuran was added 14 mL of a 1M solution of lithium hydroxide in water and the mixture was stirred at room temperature for 1 h. The reaction mixture was acidified by addition of 1M hydrochloric acid. The precipitate was collected by filtration washed with water and dried to constant weight under high vacuum to yield 2.36 g of the title compound as white solid, MS 330.3 (M−H)−.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-153393ab58854a47a2fddec0345a1d01
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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