تفاعل #1269900

معادلة التفاعل

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

paraformaldehyde

sodium cyanoborohydride

→

title compound

المردود 30.4%

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

المردود 30.4%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةat reflux for 16 h
3. 3
   workup.ADDITIONwas added
4. 4
   أخرىAfter quenching with 1 M aqueous sodium hydroxide solution (200 ml) the aqueous layer
5. 5
   استخلاصwas extracted with ethyl acetate
6. 6
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
7. 7
   تركيزconcentrated in vacuo

الإجراء التجريبي

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+).

المصدر