Hydrochloric Acid → HCID 10152588, compound

HRID 916948Notes

Reaction equation

HRID 916948 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][O:6][C:7]1[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])[N:8]=1.[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][O:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])[N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10128697HCID 10128697, compound

Product 1

HCID 10152588HCID 10152588, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(3,4-difluorobenzyloxy)-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate (150 mg, 0.28 mmol) from Example 76 in methanol (3 mL) was added 5N sodium hydroxide (0.170 mL, 0.84 mmol). The reaction was stirred at rt for 20 h and then at 40° C. for 2 h. The reaction was diluted with water, acidified with 2N hydrochloric acid, and 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 yield crude 2-(3,4-difluorobenzyloxy)-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylic acid. HPLC/MS: 520 (M+1), 522 (M+3); Rt=4.61 min.

Workup

  1. waitat 40° C. for 2 h
  2. extractionextracted twice with methylene chloride
  3. washThe organic layers were washed with a portion of brine
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9254492e37014a25b720935e85bacaae
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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