Sodium Hydroxide → 6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)pyridine-2-carboxylic acid

HRID 916960Notes

Reaction equation

HRID 916960 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]([O:17]C)=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10126602Methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-2-carboxylate

Product 1

HCID 694160556-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-2-carboxylate (300 mg, 0.76 mmol) from Example 95, Step E in methanol (6 mL) was added 5N sodium hydroxide (0.300 mL, 1.5 mmol). The reaction was stirred at rt for 20 h and was then concentrated in vacuo. The residue was partitioned between methylene chloride and 2N hydrochloric acid. The organic layer was washed with brine, dried over sodium sulfate, and evaporated to give the crude title compound as a yellow foam. HPLC/MS: 378 (M+1), 380 (M+3); Rt=3.73 min

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe residue was partitioned between methylene chloride and 2N hydrochloric acid
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4811587917fb4eeea48457306e25e35a
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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