Water → 2-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

HRID 1178576ノート

反応式

HRID 1178576 の反応式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[C:15]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:19])[CH:14]=[CH:13][N:12]=1.O>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[C:1]([NH:10][C:11]1[CH:16]=[C:15]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:19])[CH:14]=[CH:13][N:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 219641952-(2-Amino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

生成物 1

HCID 219642602-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone収率 57%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
70 °C

実験手順

Benzoyl chloride (4.4 g, 31 mmol) and 4-dimethylaminopyridine (0.57 g, 4.7 mmol) were added to a solution of 2-(2-amino-4-pyridyl)-1-(4-methoxyphenyl)ethanone (3.8 g, 16 mmol) in N,N-dimethylacetamide (80 mL) and the mixture was stirred at 70° C. for 12 hours. After the reaction mixture was cooled to room temperature, water (50 mL) was added. The mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride. The layer was dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in tetrahydrofuran (80 mL) and methanol (20 mL) and 1N-aqueous solution of sodium hydroxide (50 mL) was added. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and water (100 mL) was added. The mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride. The layer was dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain 3.1 g of the title compound (8.9 mmol, yield 57%).

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialThe layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in tetrahydrofuran (80 mL)
  8. additionmethanol (20 mL) and 1N-aqueous solution of sodium hydroxide (50 mL) was added
  9. stirringThe mixture was stirred at room temperature for 3 hours
  10. concentrationThe reaction mixture was concentrated
  11. additionwater (100 mL) was added
  12. extractionThe mixture was extracted with ethyl acetate
  13. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  14. dry with materialThe layer was dried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe residue was recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-e8e3d50861134be38e4efb07c79cfa8c
出典データセット
uspto-grants-2007_10
特許番号
US07276527B2

反応ノート

読み込み中…