Trifluoroacetic acid → 6-(2-(3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To 6-(2-(3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)ethyl)-1-(4-methoxybenzyl)-3,4-dihydroquinolin-2(1H)-one (0.06 g 0.011 mmol) was added TFA (0.13 g, 0.11 mmol) and anisole (0.012 mmol). The resulting reaction mixture was heated to 60° C. for 4 h. TFA and anisole were removed under vacuum and the crude material was washed with hexane and diethyl ether to afford 6-(2-(3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one as a brown solid (19.2 mg, 41%). 1HNMR: 400 MHz, DMSO-d6: δ 2.45 (q, J=7.20 Hz, 2H), 2.84 (t, J=7.60 Hz, 2H), 2.99 (t, J=7.60 Hz, 2H), 3.17 (t, J=7.60 Hz, 2H), 6.77 (d, J=7.60 Hz, 1H), 7.03 (t, J=1.20 Hz, 1H), 7.10 (s, 1H), 7.40 (dd, J=2.40, 8.80 Hz, 1H), 7.57 (d, J=8.80 Hz, 1H), 7.70 (d, J=2.40 Hz, 1H), 10.00 (s, 1H), 10.23 (s, 1H). LCMS: RT 2.023 min; LCMS (ES-API), m/z 401.0 [M−H]−.

Provenance & Evidence