Sodium Hydroxide → 6-Chloro-4-(2-chloro-phenyl)-nicotinic acid

HRID 1835331Notes

Reaction equation

HRID 1835331 reaction equation
C([O:3][C:4](=[O:19])[C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:9][C:8]([Cl:18])=[N:7][CH:6]=1)C.O1CCOCC1.[OH-].[Na+]>O>[Cl:18][C:8]1[CH:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:5]([C:4]([OH:19])=[O:3])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 878903116-Chloro-4-(2-chloro-phenyl)-nicotinic acid ethyl ester

Product 1

HCID 235028066-Chloro-4-(2-chloro-phenyl)-nicotinic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.20 g (10.8 mmol) 6-chloro-4-(2-chloro-phenyl)-nicotinic acid ethyl ester, 50 ml dioxane and 50 ml of a 2 M aqueous sodium hydroxide solution was stirred at room temperature for 17 h. Dilution with water was followed by washing with two portions of tert-butyl methyl ether. The combined organic layers were extracted with 1 M aqueous sodium hydroxide solution. The combined aqueous layers were acidified to pH 2 with 2 M aqueous hydrochloric acid solution and extracted with four portions of tert-butyl methyl ether. The combined organic extracts were dried with sodium sulfate and concentrated to give 2.90 g (100%) of the title compound as an off-white solid.

Workup

  1. washby washing with two portions of tert-butyl methyl ether
  2. extractionThe combined organic layers were extracted with 1 M aqueous sodium hydroxide solution
  3. extractionextracted with four portions of tert-butyl methyl ether
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-83fbcf6eda7a496387864b9c4db9f2ca
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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