Sodium Hydroxide → 3-({6-[(3-Chloropyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoic acid

HRID 1843693Notes

Reaction equation

HRID 1843693 reaction equation
[Cl:1][C:2]1[C:3]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=4)[C:22]([O:24]C)=[O:23])[N:14]([CH3:29])[C:13]=3[CH:30]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=4)[C:22]([OH:24])=[O:23])[N:14]([CH3:29])[C:13]=3[CH:30]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66705784Methyl 3-({6-[(3-chloropyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate

Product 1

HCID 469087223-({6-[(3-Chloropyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoic acidYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-({6-[(3-chloropyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate produced in Example (1f) (2.46 g, 5.8 mmol), a 2 M sodium hydroxide aqueous solution (10 mL) and 1,4-dioxane (20 mL) were stirred at 80° C. for two hours. After leaving to cool, the reaction mixture was concentrated and water (100 mL) was added. This aqueous solution was neutralized by adding 1 M hydrochloric acid and the precipitated solid was collected by filtration to obtain the title compound (1.59 g, 67%) as a white solid.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. concentrationthe reaction mixture was concentrated
  4. additionwater (100 mL) was added
  5. additionby adding 1 M hydrochloric acid
  6. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-4c2bb4920da7407c99113980c29a39a9
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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