反応 #1796879

反応方程式

ethyl acetate

2,6-dichloro-4-nitroaniline

sodium acetate

1,3-dimethoxyoctahydroisobenzofuran

→

2-(2,6-dichloro-4-nitrophenyl)-4,5,6,7-tetrahydroisoindole

溶媒

acetic acid

water

acetic acid

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to refluxing
3. 3
   温度The reaction mixture is heated
4. 4
   温度under reflux for 16 hours
5. 5
   抽出The aqueous layer is extracted with ethyl acetate
6. 6
   洗浄the combined organic layers are washed with water and with brine
7. 7
   その他dried
8. 8
   その他The residue is purified by column chromatography

実験手順

To a mixture of sodium acetate (14.0 g) in 225 ml of acetic acid heated to refluxing is first added 2,6-dichloro-4-nitroaniline (6.40 g, 30.8 mmol), followed by 1,3-dimethoxyoctahydroisobenzofuran (5.73 g, 30.8 mmol). The reaction mixture is heated under reflux for 16 hours, after which the acetic acid is stripped off by rotoevaporation and the residue is poured into ethyl acetate and water. The aqueous layer is extracted with ethyl acetate, and the combined organic layers are washed with water and with brine and dried. The residue is purified by column chromatography to give 2-(2,6-dichloro-4-nitrophenyl)-4,5,6,7-tetrahydroisoindole, which is then reduced with stannous chloride according to Example 9 procedures to give 3,5-dichloro-4-(4,5,6,7-tetrahydroisoindol-2-yl)aniline.

出典