Water → HCID 69255136, compound

HRID 1244816Notes

Reaction equation

HRID 1244816 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([CH2:30][CH3:31])[C:21]([NH:23][C:24]([CH3:29])([CH3:28])[C:25]#[C:26][CH3:27])=[O:22].O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:20]([CH2:30][CH3:31])[C:21]([NH:23][C:24]([CH3:29])([CH3:28])[C:25]#[C:26][CH3:27])=[O:22])=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 210784062-bromo-N-(4-methylpent-2-yn-4-yl)butyramideHCID 219231263-Chloroquinolin-6-ol

Product 1

HCID 69255136HCID 69255136, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a stirred mixture of 3-chloro-6-hydroxyquinoline (0.130 g) and anhydrous potassium carbonate (0.110 g) in dry N,N-dimethylformamide (3 ml) at 80° C. was added 2-bromo-N-(4-methylpent-2-yn-4-yl) butyramide (0.197 g) and the reaction maintained at this temperature for 6 hours. The brown suspension produced was cooled to ambient temperature, poured into water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulphate then evaporated under reduced pressure to give a brown gum. The gum was fractionated by chromatography (silica; hexane/ethyl acetate 4:1 by volume) to give 2-(3-chloro-6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide (0.167 g) as a colourless solid, m.p. 105–107° C., 1H NMR (CDCl3) δ: 1.08(3H, t); 1.58 (3H, s); 1.59(3H, s); 1.77(3H, s); 1.99–2.08(2H, m); 4.55(1H, t); 6.37(1H, s); 7.02(1H, d); 7.41(1H, dd); 8.01(1H, d); 8.02(1H, d); 8.70(1H, m); 8.78(1H,m).

Workup

  1. temperaturethe reaction maintained at this temperature for 6 hours
  2. customThe brown suspension produced
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customthen evaporated under reduced pressure
  7. customto give a brown gum

Sources & evidence

ORD record
ord-659227de65bf4e5da0648e72894d3fd2
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

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