反応 #82741

反応方程式

charcoal

5-nitroacenaphthene

→

clean material

5-Aminoacenaphthene

溶媒

methylene chloride

tetrahydrofuran

acetic acid

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   ろ過the mixture was filtered through a bed of celite
3. 3
   濃縮the filtrate concentrated in vacuo
4. 4
   その他to give
5. 5
   workup.ADDITIONa mixture of a solid which
6. 6
   その他the product recrystallized from a mixture of cyclohexane:ethyl acetate (3:1)

実験手順

40 gms (Aldrich lot #CY 02301 HX, containing 15% of the 3-nitro isomer) of 5-nitroacenaphthene was dissolved in a mixture of tetrahydrofuran (150 ml) and acetic acid (25 ml.). To this solution was added 1.0 of 10% Pd/C and the mixture hydrogenated (40 psi) at room temperature. After 2 hours, the mixture was filtered through a bed of celite and the filtrate concentrated in vacuo to give a mixture of a solid which darkened (to purple) considerably on exposure to air. This material was redissolved in methylene chloride and decolorized with activated charcoal and then the product recrystallized from a mixture of cyclohexane:ethyl acetate (3:1) to give 8.3 g of clean material--only the major 5-amino isomer being present by TLC. This material was used as is directly in the next step.

出典