反応 #62937

反応方程式

4,5-dihydrooxazolo[5,4-f]quinolin-2-amine

1-iodopropane

→

(±) 4,5,5a,6,7,8-hexahydro-6-propyloxazolo [5,4-f]quinolin-2-amine

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他The volatiles are then removed in-vacuo
2. 2
   洗浄the resulting solid is washed with diethyl ether
3. 3
   その他dried
4. 4
   workup.DISSOLUTIONThe resulting 2-amino-4,5-dihydrooxazolo[5,4-f]quinolinium iodide is dissolved in 150 ml of water
5. 5
   workup.ADDITIONtreated with sodium borohydride, 1.7 g (50 mmol), in small portions
6. 6
   workup.STIRRINGthe mixture is stirred for another hour
7. 7
   その他The volatile components are removed in-vacuo
8. 8
   その他the residue is partitioned between chloroform and 1% ammonium hydroxide
9. 9
   抽出The organic extract
10. 10
    濃縮is concentrated
11. 11
    その他purified by column chromatography

実験手順

A solution of 4,5-dihydrooxazolo[5,4-f]quinolin-2-amine, 5.0 g (26.7 mmol), (Example 27), in 200 ml of acetonitrile is refluxed with 1-iodopropane, 10.2 g (60 mmol), for 24 hours. The volatiles are then removed in-vacuo and the resulting solid is washed with diethyl ether and dried. The resulting 2-amino-4,5-dihydrooxazolo[5,4-f]quinolinium iodide is dissolved in 150 ml of water and treated with sodium borohydride, 1.7 g (50 mmol), in small portions. The mixture is stirred at room temperature for 2 hours. Following acidification with 10% hydrochloric acid, the mixture is stirred for another hour. The volatile components are removed in-vacuo and the residue is partitioned between chloroform and 1% ammonium hydroxide. The organic extract is concentrated and purified by column chromatography to give (±) 4,5,5a,6,7,8-hexahydro-6-propyloxazolo [5,4-f]quinolin-2-amine.

出典