反应 #1269900

反应方程式

1-bromo-8-chloro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene

paraformaldehyde

sodium cyanoborohydride

→

title compound

收率 30.4%

1-Bromo-8-chloro-5-methyl-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzoazulene

收率 30.4%

溶剂

methanol

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度at reflux for 16 h
3. 3
   workup.ADDITIONwas added
4. 4
   其他After quenching with 1 M aqueous sodium hydroxide solution (200 ml) the aqueous layer
5. 5
   萃取was extracted with ethyl acetate
6. 6
   干燥The organic layer was dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated in vacuo

实验过程

A mixture of 1-bromo-8-chloro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (1.9 g, 6.4 mmol) and paraformaldehyde (1.5 g, 51 mmol) in methanol (64 ml) was heated at reflux for 16 h. After cooling to 0° C. sodium cyanoborohydride (0.8 g, 13 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. After quenching with 1 M aqueous sodium hydroxide solution (200 ml) the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Flash chromatography over aminopropyl-modified silica gel with n-heptane/ethyl acetate as eluent gave the title compound (0.61 g) as white solid with a purity of ca. 85% as assessed by 1H-NMR. MS m/e: 313 (M+H+).

来源