Hydrochloric Acid → 4-(4-Chloro-2-fluorophenyl)-6-methylnicotinic acid

HRID 1398425Notes

Reaction equation

HRID 1398425 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=2)=[C:4]([F:19])[CH:3]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=2)=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86695958Methyl 4-(4-chloro-2-fluorophenyl)-6-methylnicotinate

Product 1

HCID 867104124-(4-Chloro-2-fluorophenyl)-6-methylnicotinic acidYield 69.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4-(4-chloro-2-fluorophenyl)-6-methylnicotinate (700 mg, 2.50 mmol) in MeOH (5 mL) was added NaOH (200 mg, 7.51 mmol) in water (5 mL). The reaction mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure and the residue obtained was adjusted to pH ˜3 by adding 1.5N HCl. The reaction mixture was extracted with dichloromethane. The organic phase was dried over Na2SO4, and concentrated under reduced pressure to afford 4-(4-chloro-2-fluorophenyl)-6-methylnicotinic acid (500 mg, 1.730 mmol, 92% crude yield) as white solid. The material was carried forward without further purification. LC/MS (ESI) m/e 266.0 [(M+H)+, calcd for C13H10ClFNO2 266.03]; LC/MS (Method I) tR=1.51 min.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue obtained
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d813ec5df95c4439b257e461f6c4e9f9
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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