Reaktion #2320131

Reaktionsgleichung

hydroxylamine hydrochloride

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

→

5,6-dihydrobenzo[h]quinoline

Ausbeute 48.3%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle