Réaction #685951

Équation de réaction

2-Acetyl-7-methoxy-3,4-dihydro-2H-naphthalen-1-one

4-benzyloxyphenylhydrazine hydrochloride

→

desired product

Rendement 32.1%

1-(4-Benzyloxyphenyl)-8-methoxy-3-methyl-4,5-dihydro-1H-benzo[g]indazole

Rendement 32.1%

Solvants

water

ethanol

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   LavageThe organic extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine
3. 3
   Séchagedried over MgSO4
4. 4
   Concentrationconcentrated

Mode opératoire

2-Acetyl-7-methoxy-3,4-dihydro-2H-naphthalen-1-one (72.5 mg, 0.33 mmol) and 4-benzyloxyphenylhydrazine hydrochloride (90 mg, 0.36 mmol) were heated in ethanol at 70° C. for 2.5 days. The reaction was diluted with water and extracted with ethyl acetate. The organic extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine, dried over MgSO4, and concentrated. SiO2 chromatography with 5-20% ethyl acetate/hexanes gave 42 mg of the desired product. LC-MS (C26H24N2O2 calculated 396) m/z 397 (M+H).

Source