6-Hydroxyquinoline → 2-(6-quinolinyloxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

HRID 1244810Notes

Reaction equation

HRID 1244810 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH2:29][O:30][CH3:31])[C:20]([NH:22][C:23]([CH3:28])([CH3:27])[C:24]#[C:25][CH3:26])=[O:21]>CN(C)C=O.O>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][CH:19]([CH2:29][O:30][CH3:31])[C:20]([NH:22][C:23]([CH3:28])([C:24]#[C:25][CH3:26])[CH3:27])=[O:21])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 113746-HydroxyquinolineHCID 11430Potassium CarbonateHCID 210784052-bromo-3-methoxy-N-(4-methylpent-2-yn-4-yl)propionamide

Product 1

HCID 219231322-(6-quinolinyloxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamideYield 29.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

6-Hydroxyquinoline (0.083 g), anhydrous potassium carbonate (0.087 g) and 2-bromo-N-(4-methylpent-2-yn-4-yl) 3-methoxypropionamide (0.150 g) in dry N,N-dimethylformamide (3 ml) were stirred and heated to 80° C. for 5 hours then stored for 72 hours at ambient temperature. The yellow suspension was diluted with water, extracted with ethyl acetate and the organic phase was separated then washed with water, dried over magnesium sulphate and evaporated under reduced pressure to a gum. The gum was fractionated by chromatography (silica; ethyl acetate:hexane, 3:2 by volume) to give the required product (0.055 g) as a colourless gum.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was separated
  3. washthen washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure to a gum

Sources & evidence

ORD record
ord-3288d4348b154b8ea51222f7197a94fc
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

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