Hydrochloric Acid → 2-[2-(Trifluoromethyl)phenyl]-3H-imidazo[4,5-c]pyridine-7-carboxylic acid

HRID 85144Notes

Reaction equation

HRID 85144 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([F:24])([F:23])[F:22])[NH:12][C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5])C.Cl>[OH-].[Na+].C(O)C>[F:24][C:21]([F:22])([F:23])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[NH:12][C:8]2[CH:9]=[N:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]=2[N:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 672030302-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine-7-carboxylic acid ethyl ester

Product 1

HCID 672044002-[2-(Trifluoromethyl)phenyl]-3H-imidazo[4,5-c]pyridine-7-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-(2-Trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine-7-carboxylic acid ethyl ester (80; 2.35 g, 7 mmol) was taken up in 10% aqueous NaOH (40 mL) and ethanol (20 mL). The reaction mixture was stirred under reflux for 30 min. Upon cooling to room temperature, the reaction mixture was acidified with 5N HCl. The resulting yellow solids were collected by filtration, washed with water, and dried to afford 2-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine-7-carboxylic acid 81 (1.77 g, 85%).

Workup

  1. temperatureunder reflux for 30 min
  2. filtrationThe resulting yellow solids were collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2ecdf8d9e0bd4a57b471a76896c109d5
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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