Hydrochloric Acid → 2-(5-Chloro-2-fluorophenyl)-6-methylisonicotinic acid

HRID 1522553Notes

Reaction equation

HRID 1522553 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([CH3:18])[N:17]=2)[C:11]([O:13]C)=[O:12])[CH:7]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([CH3:18])[N:17]=2)[C:11]([OH:13])=[O:12])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67469548HCID 67469548, compound

Product 1

HCID 674695282-(5-Chloro-2-fluorophenyl)-6-methylisonicotinic acidYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-(5-chloro-2-fluorophenyl)-6-methylisonicotinate (1.86 g, 6.65 mmol) was dissolved in methanol (24 mL) and NaOH (16.6 ml, 33.3 mmol) was added. The reaction was heated at 60° C. for 1.5 hour, cooled to room temperature, acidified (pH˜2) with 6N HCl to give a precipitate which was filtered and dried to give 2-(5-chloro-2-fluorophenyl)-6-methylisonicotinic acid (1.17 g) as a off white solid which was used without further purification. ESI-MS: m/z 266.1 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. customto give a precipitate which
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-8c9864c03a274e97ad5fc7ec4fb721ad
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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