反応 #62928

反応方程式

2,3,4,6,7,8-hexahydro-5(1H)-quinolinone

Hydrogen

→

decahydro-5-quinolinol

収率 36.2%

溶媒

acetic acid

反応条件

後処理

1. 1
   ろ過The sample was filtered
2. 2
   濃縮concentrated (
3. 3
   その他to remove most of the acetic acid),
4. 4
   抽出extracted three times with 500 ml of methylene chloride
5. 5
   抽出The combined methylene chloride extract
6. 6
   乾燥was dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

The procedure of Grob et al. (Helv. Chim. Acta 1965, 48, 799-808) was followed. A solution of 66.70 g (0.441 mol) of 2,3,4,6,7,8-hexahydro-5(1H)-quinolinone in 250 ml of glacial acetic acid containing 2 g of PtO2 was hydrogenated at 450 psi and 50° C. for 75 hours. Hydrogen uptake was only 57.2% of the theoretical. The sample was filtered, concentrated (to remove most of the acetic acid), cooled to 0° C., basified with 6N sodium hydroxide to a pH of 12 and extracted three times with 500 ml of methylene chloride. The combined methylene chloride extract was dried over magnesium sulfate, filtered and concentrated to give 24.80 g (36.2%) of decahydro-5-quinolinol, which was a three component isomeric mixture by gas chromatography (GC) analysis, as a light brown oily-solid. This mixture was carried on to the next step without further purification.

出典