Sodium Hydroxide → HCID 178422884, compound

Participants

Reaction Steps

A mixture of 7-(1H-imidazol-4-yl-methylene)-2-methyl-6,7-dihydro-5H-quinolin-8-one (Intermediate 200A4) (23.8 g, 99 mmol) in trifluoroacetic acid (120 mL) was hydrogenated under 50 psi of hydrogen in the presence of 70% perchloric acid (8 mL) and platinum oxide (12 g) for 16 h at rt. The mixture was filtered through a bed of celite, washed with ethyl acetate and evaporated to leave a residue. The residue was diluted with chloroform:isopropanol (3:1), basified with 2 M NaOH and the aqueous layer was extracted with chloroform:isopropanol (3:1). The organic layers were pooled and evaporated to give the crude product. This material was purified by chromatography on SiO2 with 3 to 4% NH3-MeOH: CH2Cl2 to give 7-(1H-imidazol-4-ylmethyl)-2-methyl-5,6,7,8-tetrahydro-quinoline (Intermediate 200A5) as a slightly yellow solid, 5.16 g (23%).

Provenance & Evidence