Methanol → 1-(3-chloro-2-pyridinyl)-3-methyl-1H-pyrazole-5-carboxylic acid

HRID 2427059노트

반응식

HRID 2427059 반응식
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]([CH3:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.CO.[OH-].[Na+]>O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([CH3:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66854396ethyl 1-(3-chloro-2-pyridinyl)-3-methyl-1H-pyrazole-5-carboxylate

생성물 1

HCID 668538491-(3-chloro-2-pyridinyl)-3-methyl-1H-pyrazole-5-carboxylic acid수율 89.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 0.30 g of ethyl 1-(3-chloro-2-pyridinyl)-3-methyl-1H-pyrazole-5-carboxylate, 5 ml of methanol and 5 ml of a 2N aqueous sodium hydroxide solution was heated to reflux for 3 hours. After the reaction mixture was allowed to cool, water was poured and the aqueous layer was washed with methyl t-butyl ether two times. The aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid, and then extracted with methyl t-butyl ether three times. The combined organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.24 g of 1-(3-chloro-2-pyridinyl)-3-methyl-1H-pyrazole-5-carboxylic acid of the formula:

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool
  4. washthe aqueous layer was washed with methyl t-butyl ether two times
  5. additionThe aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid
  6. extractionextracted with methyl t-butyl ether three times
  7. washThe combined organic layer was washed with an aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6bcc109377424b11a1757ddb24f8d729
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968573B2

반응 노트

불러오는 중…