氯化亚锡 → 5-(3-Aminophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

HRID 1069082笔记

反应方程式

HRID 1069082 反应方程式
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)[CH:6]=1)=[O:4].[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[CH:6]=1)=[O:4]

参与物

5

反应物 3

HCID 24479氯化亚锡HCID 516892碳酸氢钠HCID 545606555-(3-Nitrophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

产物 1

HCID 697796895-(3-Aminophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester收率 80.4%

试剂、催化剂与溶剂 1

HCID 8857乙酸乙酯溶剂

实验过程

5-(3-Nitrophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester (650 mg) and tin(II) chloride (2.3 g) in ethyl acetate (28 mL) were heated at 70° C. for 16 h. The mixture was allowed to cool and poured onto ice. The pH was adjusted to 7-8 by addition of saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, treated with charcoal and dried over sodium sulfate. Filtration and removal of solvent afforded the title compound as an oil (470 mg). Electrospray MS (positive ion): (M+H) 270.4.

后处理

  1. temperatureto cool
  2. additionpoured onto ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. additiontreated with charcoal
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and removal of solvent

来源与证据

ORD记录
ord-5718ecf11b0a46a3b4f1f8314bd2d881
来源数据集
uspto-grants-2001_06
专利号
US06251925B1

反应笔记

加载中…