Hydrochloric Acid → HCID 69417551, compound

HRID 916928Notes

Reaction equation

HRID 916928 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[N:4]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:5]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10172313HCID 10172313, compound

Product 1

HCID 69417551HCID 69417551, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(methoxy)-6-(4-chlorophenyl)-5-(phenyl)pyridine-3-carboxylate (150 mg, 0.42 mmol) from Example 5 in methanol (5 mL) was added 5N sodium hydroxide (0.42 mL, 2.1 mmol). The reaction was stirred at rt for 72 h and was then diluted with water and acidified with 2N hydrochloric acid. The mixture was extracted twice with methylene chloride. The organic layers were washed with a portion of brine and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title product as a white solid.

Workup

  1. extractionThe mixture was extracted twice with methylene chloride
  2. washThe organic layers were washed with a portion of brine
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e79c26aeac7640bd8757630810509910
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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