2-(Chloromethyl)quinoline → 4,5-Dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-2-(2-pyridyl)-1,3-oxazole

HRID 2352346Notes

Reaction equation

HRID 2352346 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.C[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 203942-(Chloromethyl)quinolineHCID 10942334Sodium MethoxideHCID 139142643-[2-(Pyridin-2-yl)-4,5-dihydro-1,3-oxazol-5-yl]phenol

Product 1

HCID 139142654,5-Dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-2-(2-pyridyl)-1,3-oxazoleYield 21.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,5-dihydro-5-(3-hydroxyphenyl)-2-(2-pyridyl)-1,3-oxazole (7.3 g, 0.03 mol) and 2-(chloromethyl)quinoline (5.4 g, 0.03 mol) in dimethylformamide (200 ml) is heated to 90° for 16 hours in the presence of sodium methoxide (1.6, 0.03 mol). The mixture is dissolved in ethyl acetate and water. The aqueous layer is extracted twice with ethyl acetate. The combined ethyl acetate solutions are washed twice with dilute aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to obtain an oil. This material is chromatographed on a Water Prep Pak 500 silica column with methylene chloride/methanol 99/1 (v/v) as mobile phase to obtain 2.5 g of purified material as a viscous oil.

Workup

  1. extractionThe aqueous layer is extracted twice with ethyl acetate
  2. washThe combined ethyl acetate solutions are washed twice with dilute aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain an oil
  6. customThis material is chromatographed on a Water Prep Pak 500 silica column with methylene chloride/methanol 99/1 (v/v) as mobile phase

Sources & evidence

ORD record
ord-6fcdd518d6ed47528dda0de17234a27f
Source dataset
uspto-grants-1989_10
Patent number
US04876346

Reaction notes

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