乙酐 → N-(6-chloro-3-nitropyridin-2-yl)acetamide

HRID 1823507

反应方程式

HRID 1823507 反应方程式
[H-].[Na+].[NH2:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>O1CCCC1>[Cl:13][C:6]1[N:5]=[C:4]([NH:3][C:14](=[O:16])[CH3:15])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

参与物

5

反应物 3

HCID 7918乙酐HCID 24758氢化钠HCID 27240352-氨基-3-硝基-6-氯吡啶

产物 1

HCID 2783822N-(6-chloro-3-nitropyridin-2-yl)acetamide收率 8.2%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂3 次

实验过程

To a suspension of sodium hydride (120 mg, 5 mmole) in tetrahydrofuran(10 ml), a solution of 2-amino-3-nitro-6-chloropyridine (870 mg, 5 mmole) in 20 ml of tetrahydrofuran (20 ml) was added. The reaction mixture was stirred at room temperature for 30 min. A solution of acetic anhydride (377 μl, 6 mmole) in tetrahydrofuran (10 ml) was added and stirred at room temperature overnight. The reaction mixture was quenched with water and concentrated under reduced pressure. The crude product was dissolved in dichloromethane and washed with brine. The organic layer was dried with sodium sulfate and then concentrated under vacuo. The crude was purified by flash chromatography, eluting 78% hexane:22% ethyl acetate to give a yellow product (88 mg).

后处理

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude product was dissolved in dichloromethane
  5. washwashed with brine
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated under vacuo
  8. customThe crude was purified by flash chromatography
  9. washeluting 78% hexane

来源与证据

ORD记录
ord-570f5d7a808e433bb52f75a4fda83ea1
来源数据集
uspto-grants-2006_05
专利号
US07037918B2

关联笔记

加载中…