반응 #1994248

ord-07110f227e0846ceb5ccfe957153c8c7

반응 방정식

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

용매

반응 조건

온도
0°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.STIRRINGAfter stirring for 2 h
  2. 2
    기타The solvent is then removed
  3. 3
    세척the resultant residue is washed vigorously with water
  4. 4
    기타recrystallised from dioxane
  5. 5
    여과The precipitate is filtered
  6. 6
    기타dried in vacuo

실험 절차

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%.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08597798B2uspto-grants-2013_12