Material was purified using as a yellow oil (15.4 mg, (50 toluene) CDCl3 ) 7.22.14 (m, 4H), 6.96.85 (m, 4H), a yellow oil (ten.8 mg, 55 1 H NMR (400 MHz,affording 10-methyl-9,3-Chloro-5-hydroxybenzoic acid site 10-dihydroacridine 55 as3.89 (s, 2H), three.38 (s, 10 ) 3H); 13 C NMR (101 MHz, CDCl3 ) 143.eight, 127.7,yellow 124.five, 120.7, 112.0, 33.four, 33.three ATR-IR benzyl-N-methylaniline 56 as a 127.0, oil (15.4 mg, 14 ). max (neat)/cm-1 2922, 1635, 1595, 1494, 1460, 1367, 1178, 752; GC-MS [m/z ] (14.37 min): 55 1H NMR (400 MHz, CDCl3) 7.22 7.14 (m, 4H), 6.96 six.85 (m, 4H), three.89 (s, 2H 194 (one hundred, [M-H]), 176 (42), 152 (14), 126 (4), 97 (9), 63 (10). Analytical information are in agreement (s, 3H); the literature MHz, with these reported in13C NMR (101[74]. CDCl3) 143.8, 127.7, 127.0, 124.5, 120.7, 112.0, 33.four, 33.three 56 1 H NMR (400 max (neat)/cm-1 2922, 1635, 1595, 1494, 1460,(m, 2H), 7.16752; JGC-MS [m/z ] IR MHz, CDCl3 ) 7.32.26 (m, 2H), 7.24.18 1367, 1178, (d, = 7.three Hz, 2H), 7.05.00 (d, J = 7.1 Hz, 1H), 6.77 (t, J = 7.4 Hz, 1H), 6.65 (d, J = 8.1 Hz, 1H), 3.87 (s, 2H), min): 194 (100, [M-H]), 176 (42), 152 (14), 126 (4), 97 (9), 63 (10). Analytical information 3.53 (bs, 1H), 2.77 (s, 3H); 13 C NMR (101 MHz, CDCl3 ) 147.3, 139.4, 130.6, 128.8, 128.six, agreement with those reported in max (neat)/cm-1 128.0, 126.five, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IRthe literature [74]. : 3431, 2893, 1604, 1512, 1307, 1161, 729. HRMS (ESI): calculated for3) 7.32 N 7.26 (m, ): 198.1277 7.18 (m,198.1277. (d, J = 7 56 1H NMR (400 MHz, CDCl C14 H16 ([MH] 2H), 7.24 located: 2H), 7.16 NMR data are2H), 7.05 7.00 (d, those reported within the(t, J = 7.4 Hz, 1H), 6.65 (d, J = eight.1 Hz, 1H), three in agreement with J = 7.1 Hz, 1H), 6.77 literature [75].2H), 3.53 (bs, 1H), 2.77 (s, 3H); 13C NMR (101 MHz, CDCl3) 147.3, 139.four, 130.six, 128.128.0, 126.5, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IR max (neat)/cm-1: 3431, 2893, 1604 NMR information are in agreement with these reported within the literature [75].1307, 1161, 729. HRMS (ESI): calculated for C14H16N ([MH]): 198.1277 found:2H), 7.05 7.00 (d, J = 7.1 Hz, 1H), 6.77 (t, J = 7.four Hz, 1H), 6.65 (d, J = 8.1 Hz, 1H),2H), 3.53 (bs, 1H), two.77 (s, 3H); 13C NMR (101 MHz, CDCl3) 147.three, 139.four, 130.six, 128.Molecules 2021, 26,128.0, 126.five, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IR max (neat)/cm-1: 3431, 2893, 1604 NMR information are in agreement with these reported in the literature [75].3.3.four. Reaction three.3.four. Reaction of N,