Hydrochloric Acid → HCID 69415176, compound

HRID 916942Notes

Reaction equation

HRID 916942 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([O:17]C)=[O:16])=[CH:13][C:12]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[CH2:1]([O:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[C:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 44390743HCID 44390743, compound

Product 1

HCID 69415176HCID 69415176, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(benzyloxy)-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate (390 mg, 0.78 mmol) from Example 51, Step B in methanol (5 mL) was added 5N sodium hydroxide (0.31 mL, 1.56 mmol). The reaction was stirred at rt 20 h and then at 40° C. for 1 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 give crude 2-(benzyloxy)-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylic acid.

Workup

  1. waitat 40° C. for 1 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-093a9662b5ed4849ba94f154c6bef239
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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