六水硝酸铽 → 5-硝基-1H-吲唑-3羧酸乙酯

HRID 600654

反应方程式

HRID 600654 反应方程式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:2]1.[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[N+:15]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[C:3]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-:17])=[O:16]

参与物

4

反应物 2

HCID 944六水硝酸铽HCID 78251吲唑-3-羧酸乙脂

产物 1

HCID 126893685-硝基-1H-吲唑-3羧酸乙酯收率 53%

试剂、催化剂与溶剂 1

HCID 1118四氧化硫溶剂2 次

反应条件

温度
0 °C

实验过程

Ethyl indazole-3-carboxylate (73.7 mmol) was dissolved in 20 mL concentrated sulfuric acid and the reaction mixture was cooled to 0° C. A mixture of concentrated sulfuric acid (12 mL) and 70% nitric acid (12 mL) was added dropwise over the course of 1 h. The mixture was stirred for an additional 1 h at 0° C. and was poured onto of crushed ice (200 g). The solid was collected by vacuum filtration, washed with several portions of water and dried in vacuo. The dried solid was suspended in 250 mL acetonitrile and the mixture was heated at reflux for 2 h. The mixture was allowed to cool to room temperature and the solid was collected and dried in vacuo to provide ethyl 5-nitroindazole-3-carboxylate (53%) as a colorless solid. The acid, obtained by basic hydrolysis, was coupled with the bicyclobase according to procedure A.

后处理

  1. additionwas added dropwise over the course of 1 h
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with several portions of water
  4. customdried in vacuo
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 2 h
  7. temperatureto cool to room temperature
  8. customthe solid was collected
  9. customdried in vacuo

来源与证据

ORD记录
ord-5fd1762151a448b684ac8773e75c30ba
来源数据集
uspto-grants-2011_03
专利号
US07902217B2

关联笔记

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