Water → HCID 69255136、化合物

HRID 2222299ノート

反応式

HRID 2222299 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 69255136HCID 69255136、化合物収率 66.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-64c09b06f96244bd95bb1a0ca05489c8
出典データセット
uspto-grants-2008_05
特許番号
US07371764B2

反応ノート

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