Sodium Hydroxide → 2-(4-Chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime

HRID 723984ノート

反応式

HRID 723984 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=O)[CH:3]=1.Cl.[NH2:19][OH:20].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:19][OH:20])[CH:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 218740612-(4-Chloropyridin-2-yl)-1-(4-fluorophenyl)ethan-1-one

生成物 1

HCID 738517532-(4-Chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime収率 84%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (9.6 g, 38 mmol) in methanol (200 mL) was added hydroxylamine hydrochloride (13.5 g, 190 mmol) followed by the addition of a sodium hydroxide solution (7.8 g, 190 mmol in 50 mL of water). The resulting suspension was heated at reflux for 2 hours and then allowed to cool to room temperature. The mixture was concentrated and water was added to the resulting slurry. A white precipitate formed, which was collected by filtration, washed with water and dried (magnesium sulfate) to give 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime (8.45 g, 84%) as a white solid. 1H-NMR (DMSO-d6): δ 11.56 (s, 1H), 8.44 (d, 1H), 7.80 (m, 2H), 7.40 (m, 2H), 7.22 (m, 2H), 4.29 (s, 2H); 19F-NMR (DMSO-d6): δ −113.44; MS m/265 (M+1).

後処理

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe mixture was concentrated
  4. additionwater was added to the resulting slurry
  5. customA white precipitate formed
  6. filtrationwhich was collected by filtration
  7. washwashed with water
  8. dry with materialdried (magnesium sulfate)

出典と根拠

ORDレコード
ord-b8a24a5ac03f421faaf73b618c491709
出典データセット
uspto-grants-2006_11
特許番号
US07141569B2

反応ノート

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