Hydrochloric Acid → 4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester
反応式
[C:1]1([NH:7][C:8]2[C:13]([C:14](=[O:16])[CH3:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=O.Cl>CO.O>[CH3:29][O:28][C:26](=[O:27])[C:25]1[CH:30]=[CH:31][C:22](/[CH:20]=[CH:15]/[C:14](=[O:16])[C:13]2[C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:23][CH:24]=1参加物
反応条件
- 温度
- 25 °C
実験手順
A solution of 1-(2-phenylamino-pyridin-3-yl)-ethanone (2.13 g, 10.0 mmol) in methanol (42 mL, 0.24M) was treated with sodium methoxide (25% wt. solution methanol, 4.6 mL, 20.1 mmol) and methyl 4-formylbenzoate (2.04 g, 12.4 mmol). The reaction was stirred at 25° C. over 3 d. At this time, the reaction was diluted with water (100 mL), acidified with a 1N aqueous hydrochloric acid solution, and extracted with a 10% methanol/methylene chloride solution. The combined organics were dried over magnesium sulfate, filtered, rinsed with methylene chloride, and concentrated onto silica gel in vacuo. Flash chromatography (AnaLogix Intelliflash 280, 80 g silica gel column, 20% ethyl acetate/hexanes) afforded 4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester (3.43 g, 95%) as an orange solid.
後処理
- extractionextracted with a 10% methanol/methylene chloride solution
- dry with materialThe combined organics were dried over magnesium sulfate
- filtrationfiltered
- washrinsed with methylene chloride
- concentrationconcentrated onto silica gel in vacuo
出典と根拠
- ORDレコード
- ord-54dfa5cfaff0455c897d50ca211024d6
- 出典データセット
- uspto-grants-2013_06
- 特許番号
- US08471027B2
反応ノート
読み込み中…