Sodium Hydroxide → [3-Chloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-5-methyl-phenyl]-acetic acid

HRID 2199106Notes

Reaction equation

HRID 2199106 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][C:13]2[N:14]=[N:15][C:16]([Cl:22])=[C:17]([CH:19]([CH3:21])[CH3:20])[CH:18]=2)=[C:7]([Cl:23])[CH:6]=1.[OH-].[Na+]>CO>[Cl:23][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:24])=[O:2])[CH:10]=[C:9]([CH3:11])[C:8]=1[O:12][C:13]1[N:14]=[N:15][C:16]([Cl:22])=[C:17]([CH:19]([CH3:21])[CH3:20])[CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86610363[3-Chloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-5-methyl-phenyl]-acetic acid methyl ester

Product 1

HCID 86610364[3-Chloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-5-methyl-phenyl]-acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [3-chloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-5-methyl-phenyl]-acetic acid methyl ester (8b) (1.1 g, 2.97 mmol) in methanol (30 mL) at room temperature was treated dropwise with a 1N aqueous sodium hydroxide solution (5.9 mL, 5.9 mmol). The reaction was stirred at room temperature for 4 d. At this time, the reaction mixture was concentrated under vacuum. The resulting solid was diluted with water and ethyl acetate. The ethyl acetate layer was discarded. The water layer was acidified by the addition of a 1N aqueous hydrochloric acid solution and was extracted with ethyl acetate. The organic layers were washed with a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum to afford [3-chloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-5-methyl-phenyl]-acetic acid (9b) (1.05 g, 100%) as a white solid. This material was used without further purification; EI(+)-HRMS m/z calcd for C16H16Cl2N2O3 (M+) 355.0611, found 355.0610. Molecular Weight=355.2235; Exact Mass=354.0538

Workup

  1. concentrationAt this time, the reaction mixture was concentrated under vacuum
  2. additionThe resulting solid was diluted with water and ethyl acetate
  3. additionThe water layer was acidified by the addition of a 1N aqueous hydrochloric acid solution
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-441ca798fc574393bf52db6afd7d43ca
Source dataset
uspto-grants-2016_06
Patent number
USRE046024E1

Reaction notes

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