Réaction #2320131

Équation de réaction

hydroxylamine hydrochloride

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

→

5,6-dihydrobenzo[h]quinoline

Rendement 48.3%

Solvants

acetonitrile

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source