Реакция #2320131

Уравнение реакции

hydroxylamine hydrochloride

2-ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene

→

5,6-dihydrobenzo[h]quinoline

Выход 48.3%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was heated
2. 2
   Температураat reflux under nitrogen
3. 3
   ДругоеEvaporation of the acetonitrile
4. 4
   workup.DISTILLATIONfollowed by vacuum distillation of the product
5. 5
   Другоеyielded 34.5 g of a crude product that
6. 6
   Другоеwas further purified by silica gel chromatography with 5/95 ethyl acetate/hexane as the eluent

Методика

To a suspension of hydroxylamine hydrochloride (46.1 g, 0.663 mol) in 1070 mL of acetonitrile was added 2-ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene (140 g, 0.265 mol) from step two. The reaction mixture was heated at reflux under nitrogen with stirring for 16 h. Evaporation of the acetonitrile, followed by vacuum distillation of the product yielded 34.5 g of a crude product that was further purified by silica gel chromatography with 5/95 ethyl acetate/hexane as the eluent, yielding 23.2 g (45%) of 5,6-dihydrobenzo[h]quinoline as a yellow liquid.

Источник