西诺沙星 → HCID 86732789，化合物

HRID 525922笔记

反应方程式

HRID 525922 反应方程式
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]3[O:15][CH2:14][O:13][C:10]=3[CH:11]=2)[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[N:4]1)[CH3:2].[N+:20]([O-])([O-:22])=[O:21].[K+]>S(=O)(=O)(O)O>[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([N+:20]([O-:22])=[O:21])[C:9]3[O:15][CH2:14][O:13][C:10]=3[CH:11]=2)[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[N:4]1)[CH3:2]

参与物

4

反应物 2

HCID 2762西诺沙星HCID 24434硝酸钾

产物 1

HCID 86732789HCID 86732789，化合物收率 75.1%

试剂、催化剂与溶剂 1

HCID 1118四氧化硫溶剂

反应条件

温度
10 °C

实验过程

To a solution of 1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid (5 g, 19.07 mmol) in sulfuric acid (15 mL) cooled to 0° C. was added potassium nitrate (2.121 g, 20.97 mmol) in small portions to maintain temperature bellow 10° C. with ice water. The mixture was stirred at 10° C. for 1 h and at room temperature for 12 h, and was then poured into ice cold water (200 ml). The mixture was filtered, the solid was washed with water and ethanol to afford 1-ethyl-5-nitro-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid (4.4 g, 14.32 mmol, 75% yield). LCMS: (M+H)+: 308.2

后处理

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with water and ethanol

来源与证据

ORD记录
ord-c74ae039e9144f3ea0ea2c2c41c6675a
来源数据集
uspto-grants-2016_05
专利号
US09340556B2

反应笔记

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