Acetic Anhydride → HCID 9865642, compound

HRID 1884585Notes

Reaction equation

HRID 1884585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=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[OH:22])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C(OCC)(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=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[O:22][C:26](=[O:28])[CH3:27])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 9928654HCID 9928654, compound

Product 1

HCID 9865642HCID 9865642, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(3-Chlorophenoxy)-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine (1.0 g, 2.8 mmol) obtained in Example 31 is dissolved in pyridine (3 ml), and thereto is added acetic anhydride (1.3 ml, 14 mmol), and the mixture is stirred at room temperature for 5 hours. To the reaction solution is added ethyl acetate (100 ml), and the mixture is washed with a saturated brine (30 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give 2-(3-chlorophenoxy)-3-[3-(3-acetoxypyridin-4-yl)propoxy]pyridine, which is further treated with fumaric acid to give the title compound (1.07 g), m.p. 107-126° C. (recrystallized from diethyl ether).

Workup

  1. washthe mixture is washed with a saturated brine (30 ml×2)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-24054541e9c14f33bb7c6044a4001a3a
Source dataset
uspto-grants-2004_07
Patent number
US06765095B2

Reaction notes

Loading…