Material was purified utilizing 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-9,10-dihydroacridine 55 as3.89 (s, 2H), three.38 (s, ten ) 3H); 13 C NMR (101 MHz, CDCl3 ) 143.eight, 127.7,yellow 124.5, 120.7, 112.0, 33.4, 33.three ATR-IR benzyl-N-methylaniline 56 as a 127.0, oil (15.four 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), six.96 6.85 (m, 4H), 3.89 (s, 2H 194 (100, [M-H]), 176 (42), 152 (14), 126 (4), 97 (9), 63 (10). Analytical information are in agreement (s, 3H); the literature MHz, with those reported in13C NMR (101[74]. CDCl3) 143.8, 127.7, 127.0, 124.five, 120.7, 112.0, 33.4, 33.3 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, = 7.3 Hz, 2H), 7.05.00 (d, J = 7.1 Hz, 1H), 6.77 (t, J = 7.4 Hz, 1H), 6.65 (d, J = eight.1 Hz, 1H), 3.87 (s, 2H), min): 194 (one hundred, [M-H]), 176 (42), 152 (14), 126 (four), 97 (9), 63 (10). Analytical data 3.53 (bs, 1H), 2.77 (s, 3H); 13 C NMR (101 MHz, CDCl3 ) 147.3, 139.4, 130.six, 128.8, 128.6, agreement with these 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 identified: 2H), 7.16 NMR information are2H), 7.05 7.00 (d, these reported within the(t, J = 7.four Hz, 1H), 6.65 (d, J = eight.1 Hz, 1H), 3 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, 139.4, 130.6, 128.128.0, 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 inside the literature [75].1307, 1161, 729. HRMS (ESI): calculated for C14H16N ([MH]): 198.1277 located:2H), 7.05 7.00 (d, J = 7.1 Hz, 1H), six.77 (t, J = 7.4 Hz, 1H), 6.65 (d, J = eight.1 Hz, 1H),2H), three.53 (bs, 1H), two.77 (s, 3H); 13C NMR (101 MHz, CDCl3) 147.3, 139.4, 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.three.four. Reaction 3.3.4. Reaction of N,2-dimethyl-N-phenylaniline 52 with KOtBu/Et3SiH – neat: of N,2-dimethyl-N-phenylaniline 52 with KOtBu/Et3 SiH–Neat15 of identified: 198 1307, 1161, 729. HRMS (ESI): calculated for C14H16N ([MH]): 198.12773-Chloro-5-hydroxybenzoic acid Protocol Substrate 52 (99 mg, 1.0 equiv., (3.0 equiv., KOtBu (3.0 equiv., 1.5 mmol, Substrate 52 (99 mg, 1.0 equiv., 0.five mmol), KOt Bu0.5 mmol), 1.5 mmol, 168 mg), and Et3 SiH 168 mg (3.0 equiv., 1.5Et3SiH (3.0 ) had been sealed in 240 L) had been sealednitrogen-filled tube within a nitrogen mmol, 240 equiv., 1.5 mmol, a Fmoc-Gly-Gly-OH Technical Information pressure tube within a inside a pressure glovebox. The contents with the stress tube had been stirred at 130 C for 18 h just before the stress tube glovebox. The contents on the stress tube were stirred at 130 for 18 h befo was cooled to room temperature, opened to air and diluted with water (50 mL). The stress extracted into Et2 area 50 mL). The combined organic phases organic goods had been tube was cooled too (3 emperature, opened to air and diluted with wa were dried over Na2 SO4 organic merchandise had been extracted intomaterial was purified employing mL). The and concentrated in vacuo. The crude Et2O (3 x 50 mL). T.
