HCID 59490300, compound → HCID 46830641, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrile (186 mg, 0.510 mmol) in 48% hydrobromic acid (1 mL) and 33% wt hydrogen bromide in acetic acid (1 mL) was heated to 200° C. for 45 minutes under microwave irradiation. The mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was removed and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative TLC using dichloromethane-methanol (19:1) as eluent to provide 6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[f]isoquinolin-2-amine as an off-white solid (44 mg, 25%). 1H NMR 400 MHz (DMSO-d6) δ 7.80 (d, J=7.6 Hz, 1H), 7.74 (s, 1H), 7.47 (d, J=8 Hz, 1H), 7.41 (t, J=7.2 Hz, 1H), 7.34 (m, 2H), 7.07 (d, J=7.6 Hz, 1H), 6.98 (d, J=8 Hz, 1H), 6.87 (s, 1H), 5.78 (s, 2H), 4.30 (m, 1H), 2.98 (d, J=5.6 Hz, 2H). LCMS m/e 341 (M+H).

Provenance & Evidence