Sodium Bicarbonate → HCID 9843420, compound

HRID 1884590Notes

Reaction equation

HRID 1884590 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[C:21]([O:22]C)=[CH:20][N:19]=[CH:18][C:17]=2[Cl:24])=[CH:10][CH:9]=[CH:8][N:7]=1.Cl.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[C:21]([OH:22])=[CH:20][N:19]=[CH:18][C:17]=2[Cl:24])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 23506232HCID 23506232, compound

Product 1

HCID 9843420HCID 9843420, compoundYield 68.2%

Procedure

2-(3-Chlorophenoxy)-3-[3-(3-chloro-5-methoxypyridin-4-yl)propoxy]pyridine (8.5 g, 21 mmol) obtained in Example 72 and pyridine hydrochloride (100 g, 0.86 mol) are mixed, and the mixture is stirred for melting at 150° C. for one hour. To the mixture is added ice-water (300 ml), and the mixture is neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate (100 ml×3). The organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution (50 ml×2) and a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by basic silica gel column chromatography (eluent: ethanol/ethyl acetate), and further recrystallized from diethyl ether/diisopropyl ether to give the title compound (5.6 g) as colorless crystals, m.p. 95-96° C.

Workup

  1. extractionextracted with ethyl acetate (100 ml×3)
  2. washThe organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution (50 ml×2)
  3. dry with materiala saturated brine (50 ml×2), dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by basic silica gel column chromatography (eluent: ethanol/ethyl acetate)
  6. customfurther recrystallized from diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-e237cf471e234e998ed8c349a8a656fb
Source dataset
uspto-grants-2004_07
Patent number
US06765095B2

Reaction notes

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