反应 #1994248

ord-07110f227e0846ceb5ccfe957153c8c7

反应方程式

O=[N+]([O-])c1cccc2ccc(-c3ccc4ccccc4n3)cc12
8-nitro-2-naphthylquinoline
[BH4-].[Na+]
sodium borohydride
Cl
HCl
Nc1cccc2ccc(-c3ccc4ccccc4n3)cc12
crystalline solid
收率 135.5%
Nc1cccc2ccc(-c3ccc4ccccc4n3)cc12
8-Amino-2-naphthylquinoline
收率 135.5%

溶剂

反应条件

温度
0°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGAfter stirring for 2 h
  2. 2
    其他The solvent is then removed
  3. 3
    洗涤the resultant residue is washed vigorously with water
  4. 4
    其他recrystallised from dioxane
  5. 5
    过滤The precipitate is filtered
  6. 6
    其他dried in vacuo

实验过程

12.6 g (42 mmol) of 8-nitro-2-naphthylquinoline and 1.99 g of Pd/C (10%) are suspended in 200 ml of methanol. 8.4 g (222 mmol) of sodium borohydride are added in portions with stirring at 0° C. After stirring for 2 h, the clear solution is neutralised using dilute HCl. The solvent is then removed, and the resultant residue is washed vigorously with water and recrystallised from dioxane. The precipitate is filtered and dried in vacuo, giving 9.9 g (56.9 mmol) of crystalline solid. The overall yield is 88%.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08597798B2uspto-grants-2013_12