4-Methoxyphenylhydrazine hydrochloride → HCID 67196072, compound

Participants

Reaction Conditions

Reaction Steps

2-Acetyloctahydronaphthalen-1-one (0.96 g, 4.95 mmol) was dissolved in absolute ethanol (10 mL), and 4-methoxyphenylhydrazine hydrochloride (0.95 g, 5.44 mmol) was added. The reaction was stirred overnight at 70° C. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine, then dried over MgSO4 and concentrated. SiO2 chromatography with 5-40% ethyl acetate/hexanes gave 0.15 g of 2-(4-methoxyphenyl)-3-methyl-4,5,5a,6,7,8,9,9a-octahydro-2H-benzo[g]indazole and 0.66 g of 1-(4-methoxyphenyl)-3-methyl-4,5,5a,6,7,8,9,9a-octahydro-1H-benzo[g]indazole. Regiochemistry was determined by x-ray crystal structure of 1-(4-methoxyphenyl)-3-methyl-4,5,5a,6,7,8,9,9a-octahydro-1H-benzo[g]indazole. LC-MS (C19H24N2O calculated 296) m/z 297 (M+H).

Provenance & Evidence