反応 #1994248

ord-07110f227e0846ceb5ccfe957153c8c7

反応方程式

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

溶媒

反応条件

温度
0°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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%.

出典

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