Hydrochloric Acid → HCID 71666010, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-(methylthio)-2-oxo-6-(pyren-1-yl)-2H-pyran-3-carboxylate (400 mg, 1 mmol), 2-phenyl-6,7-dihydro-2H-indazol-4(5H)-one (212 mg, 1 mmol) and powdered KOH (84 mg, 1.5 mmol) in dry DMF (5 mL) was stirred at 25° C. for 8 hr. At the end the reaction mixture was poured into ice water with vigorous stirring and finally neutralized with dilute HCl. The solid thus obtained was filtered and purified on a neutral alumina column using 15% chloroform in hexane as eluent to yield 58% of methyl 8-(methylthio)-2-phenyl-6-(pyren-1-yl)-4,5-dihydro-2H-benzo[e]indazole-9-carboxylate. Yellow solid; mp-174-176° C.; 1H NMR (300 MHz, CDCl3) δ 2.49 (s, 3H, CH3), 2.60-2.67 (m, 2H, CH2), 2.71-2.77 (m, 2H, CH2), 4.08 (s, 3H, OCH3), 7.27-7.36 (m, 2H, ArH), 7.47 (t, J1=8.28 Hz, J2=7.50 Hz, 2H, ArH), 7.65-7.72 (m, 2H, ArH), 7.73-7.81 (m, 1H, ArH), 7.90 (d, J=7.77 Hz, 1H, ArH), 7.99-8.09 (m, 3H, ArH), 8.14 (s, 2H, ArH), 8.18-8.29 (m, 3H, ArH); MS (ESI) m/z551 (M++1).

Provenance & Evidence