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

HRID 251949

反応式

HRID 251949 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]([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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-f2476462d1944a7aa6900e144b3f98b7
出典データセット
uspto-grants-2011_01
特許番号
US07867949B2

関連ノート

読み込み中…