(4-Methylphenyl)hydrazine → HCID 21220552, compound

Participants

Reaction Steps

Methyl 5,6,7,8-tetrahydro-5-oxoisoquinoline-6-acetate hydrobromide (1.2 g) (Wu et al, Synthetic Communications 24, 273 (1994)) 4-tolylhydrazine (0.5 g) and 4-tolylhydrazine hydrochloride (0.19 g) in xylene (20 ml) were heated under reflux for 3 hours. The reaction mixture was allowed to cool to room temperature and the volatiles removed. The residue was dissolved in dichloromethane-methanol, washed with sodium hydrogen carbonate solution twice and then brine. The organic phase was dried, filtered and concentrated to a dark oil. The crude product was adsorbed onto silica and chromatographed eluting with 7:3 dichloromethane:ethyl acetate. The resultant oil was triturated with ether and recrystallised from isopropanol to give the title compound (0.3 g).

Provenance & Evidence