Water → 1-(3-Chloropyridin-2-yl)-3-hydroxy-1H-pyrazole-5-carboxylic acid

HRID 1445538ノート

反応式

HRID 1445538 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10](=[O:18])[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.O.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10](=[O:18])[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21113391Ethyl 2-(3-chloro-2-pyridinyl)-2,5-dihydro-5-oxo-1H-pyrazole-3-carboxylate2 回

生成物 1

HCID 685431821-(3-Chloropyridin-2-yl)-3-hydroxy-1H-pyrazole-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of ethyl 1-(3-chloro-2-pyridinyl)-2,3-dihydro-3-oxo-1H-pyrazole-5-carboxylate (i.e. the product of Step B) (1.0 g, 3.7 mmol) in methanol (15 mL) was added water (3 mL). An aqueous solution of sodium hydroxide (50%, 1.0 g, 12.5 mmol) was added dropwise, and the reaction mixture was stirred at room temperature for 3 hours, during which time the reaction mixture turned a clear yellow. Water (20 mL) was added and the reaction mixture was extracted with ethyl ether, which was discarded. The aqueous phase was acidified to pH 2 using concentrated hydrochloric acid and then extracted with ethyl acetate (50 mL). The ethyl acetate extract was washed with water (20 mL) and brine (20 mL), dried over magnesium sulfate and concentrated to give the title compound, isolated as a white solid (0.76 g).

後処理

  1. extractionthe reaction mixture was extracted with ethyl ether, which
  2. extractionextracted with ethyl acetate (50 mL)
  3. extractionThe ethyl acetate extract
  4. washwas washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-073fbd7a393747a2b3acb4b5d1c25849
出典データセット
uspto-grants-2010_02
特許番号
US07666882B2

反応ノート

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