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

HRID 1445538노트

반응식

HRID 1445538 반응식
[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

참가 물질

5

반응물 3

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21113391Ethyl 2-(3-chloro-2-pyridinyl)-2,5-dihydro-5-oxo-1H-pyrazole-3-carboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-073fbd7a393747a2b3acb4b5d1c25849
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666882B2

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