Water → 2-(6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide

HRID 1244802Notes

Reaction equation

HRID 1244802 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.[H-].[Na+].Br[CH:15]([CH2:25][CH3:26])[C:16]([NH:18][C:19]([CH3:24])([CH3:23])[C:20]#[C:21][CH3:22])=[O:17].O>CN(C)C=O.C(OCC)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][CH:15]([CH2:25][CH3:26])[C:16]([NH:18][C:19]([CH3:24])([CH3:23])[C:20]#[C:21][CH3:22])=[O:17])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 113746-HydroxyquinolineHCID 24758Sodium hydrideHCID 210784062-bromo-N-(4-methylpent-2-yn-4-yl)butyramide

Product 1

HCID 692539492-(6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

6-Hydroxyquinoline (0.46 g) in dry N,N-dimethylformamide (10 ml) was added dropwise to a stirred suspension of sodium hydride (0.10 g, 80% dispersion in mineral oil) in dry N,N-dimethylformamide under an atmosphere of nitrogen at ambient temperature. The green solution was stirred at ambient temperature for 1 hour and a solution of 2-bromo-N-(4-methylpent-2-yn-4-yl) butyramide (0.74 g) in dry N,N-dimethylformamide (10 ml) was added. The mixture was stirred at ambient temperature for 18 hours, poured into water and extracted into diethyl ether (three times). The organic extracts were combined, washed with dilute aqueous sodium hydroxide, water (twice), dried over magnesium sulphate and evaporated under reduced pressure to give a gum. The gum was fractionated by chromatography (silica; diethyl ether) to give the required product, 0.44 g, as a colourless gum.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 18 hours
  2. extractionextracted into diethyl ether (three times)
  3. washwashed with dilute aqueous sodium hydroxide, water (twice),
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customto give a gum

Sources & evidence

ORD record
ord-99db936f45e540a699132e3da49f1985
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

Loading…