Hydrochloric Acid → 3-Amino-6-(4-fluoro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid

HRID 2173723Notes

Reaction equation

HRID 2173723 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([O:21]C)=[O:20])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-].[Na+].Cl>CCO.O>[NH2:1][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[N:4][C:5]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89443105Methyl 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinate

Product 1

HCID 584423103-Amino-6-(4-fluoro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinate (step 1) (6.00 mmol) in EtOH (5 ml) was added 2M NaOH (3 ml, 6.00 mmol) and the solution was stirred at RT for 15 minutes. The resulting mixture was diluted with water (10 ml) and the pH was adjusted to pH 6 using 1M HCl. The mixture was extracted with DCM (2×10 ml) and the phases were separated using a phase separating cartridge. The combined organic extracts were concentrated in vacuo and used in the next step without further purification;

Workup

  1. extractionThe mixture was extracted with DCM (2×10 ml)
  2. customthe phases were separated
  3. customseparating cartridge
  4. concentrationThe combined organic extracts were concentrated in vacuo
  5. customused in the next step without further purification

Sources & evidence

ORD record
ord-5a2893a8d63444b4966a415a418033f2
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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