Sodium Hydroxide → HCID 12986045, compound

HRID 1841558Notes

Reaction equation

HRID 1841558 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[C:22]([O:24]CC)=[O:23])=[CH:10][CH:9]=[CH:8][N:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[C:22]([OH:24])=[O:23])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12986044HCID 12986044, compound

Product 1

HCID 12986045HCID 12986045, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Chlorophenoxy)-3-[3-(3-ethoxycarbonylpyridin-4-yl)-propoxy]pyridine (1.0 g, 2.4 mmol) obtained in Example 23 is dissolved in methanol (50 ml), and thereto is added a 1M aqueous sodium hydroxide solution (3.0 ml), and the mixture is heated under reflux for 2 hours. The methanol is evaporated under reduced pressure, and the pH value of the residue is adjusted to pH 4 with a 1M aqueous hydrochloric acid solution, and the mixture is extracted with chloroform/tetrahydrofuran (1:1) (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from ethanol/diethyl ether to give the title compound (0.9 g) as colorless crystals, m.p. 142-144° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customThe methanol is evaporated under reduced pressure
  4. extractionthe mixture is extracted with chloroform/tetrahydrofuran (1:1) (50 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is recrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-d6a019efe40040608546e7fa0b5c735c
Source dataset
uspto-grants-2004_01
Patent number
US06683186B2

Reaction notes

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