The Journal of Organic Chemistry
Page 8 of 12
NMR (101 MHz, CDCl3) δ 149.1, 148.9, 146.9, 140.4, 136.1, 130.4, 129.8, 129.5, 128.5, 128.4, 128.3, 127.9, 126.9, 126.5, 125.2,
124.8, 123.5, 22.1.
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2,9-dimethylacridine (3l) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow solid
(34.9 mg, 84%): 1H NMR (400 MHz, CDCl3) δ 8.18 (d, J = 8.8 Hz, 2H), 8.10 (d, J = 8.8 Hz, 1H), 7.92 (s, 1H), 7.74 – 7.68 (m, 1H),
7.57 (dd, J = 8.8, 2.0 Hz, 1H), 7.53 – 7.47 (m, 1H), 3.03 (s, 3H), 2.57 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 147.9, 147.3,
140.9, 135.0, 132.6, 130.2, 129.9, 129.2, 125.6, 125.5, 125.2, 124.4, 122.8, 22.2, 13.5.
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4-methyl-9-phenylacridine (3m) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow
solid (35.2 mg, 65%): 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J = 8.8 Hz, 1H), 7.76 – 7.70 (m, 1H), 7.68 – 7.63 (m, 1H), 7.61 – 7.51
(m, 5H), 7.43 – 7.36 (m, 3H), 7.29 (dd, J = 8.8, 6.8 Hz, 1H), 2.99 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 148.4, 148.1, 146.9,
137.3, 136.5, 130.5, 130.2, 129.4, 129.2, 128.4, 128.2, 126.7, 125.5, 125.4, 125.1, 124.9, 124.9, 18.7.
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4,9-dimethylacridine (3n) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow solid
(26.4 mg, 64%): 1H NMR (400 MHz, CDCl3) δ 8.27 – 8.20 (m, 2H), 8.09 (d, J = 8.8 Hz, 1H), 7.76 – 7.70 (m, 1H), 7.59 (d, J = 6.4
Hz, 1H), 7.56 – 7.50 (m, 1H), 7.42 (dd, J = 8.8, 6.8 Hz, 1H), 3.09 (s, 3H), 2.94 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 148.0,
147.7, 141.8, 137.9, 130.9, 129.2, 129.1, 125.5, 125.3, 125.2, 124.4, 122.5, 18.8, 13.8.
2-ethyl-9-phenylacridine (3o) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow
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solid (53.5 mg, 94%): H NMR (400 MHz, CDCl3) δ 8.23 (dd, J = 19.2, 8.8 Hz, 2H), 7.72 (ddd, J = 8.0, 6.4, 1.2 Hz, 1H), 7.68 –
7.62 (m, 2H), 7.63 – 7.55 (m, 3H), 7.45 – 7.41 (m, 3H), 7.38 (ddd, J = 7.6, 6.4, 1.2 Hz, 1H), 2.73 (q, J = 7.6 Hz, 2H), 1.23 (t, J =
7.6 Hz, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 148.3, 148.0, 146.2, 141.6, 136.2, 131.8, 130.5, 129.6, 129.5, 129.5, 128.5, 128.3,
126.8, 125.5, 125.3, 125.2, 123.6, 29.2, 15.2.
1-methoxy-9-methylacridine (3p) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow
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solid (14.7 mg, 33%): mp: 100-102 C; H NMR (400 MHz, CDCl3) δ 8.35 – 8.30 (m, 1H), 8.15 (dd, J = 8.7, 0.5 Hz, 1H), 7.80 –
7.71 (m, 2H), 7.60 (dd, J = 8.7, 7.6 Hz, 1H), 7.52 (ddd, J = 8.8, 6.5, 1.2 Hz, 1H), 6.77 (d, J = 7.5 Hz, 1H), 4.01 (s, 3H), 3.36 (s,
3H). 13C{1H} NMR (101 MHz, CDCl3) δ 158.0, 150.2, 148.1, 144.6, 129.9, 129.8, 129.5, 126.3, 125.1, 124.7, 122.7, 119.8, 103.1,
55.6, 18.0. HRMS (ESI) m/z: [M + H]+ calcd for C15H14NO 224.1070; found 224.1069. IR (cm-1): 3064, 2833, 1463, 1087, 752.
3-methoxy-9-methylacridine (3p’) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow
solid (29.0 mg, 65%): 1H NMR (400 MHz, CDCl3) δ 8.15 (dd, J = 15.2, 8.5 Hz, 2H), 8.08 (d, J = 9.5 Hz, 1H), 7.75 – 7.69 (m, 1H),
7.50 – 7.45 (m, 1H), 7.41 (d, J = 2.6 Hz, 1H), 7.19 (dd, J = 9.5, 2.6 Hz, 1H), 3.98 (s, 3H), 3.03 (d, J = 7.6 Hz, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 161.0, 150.2, 148.5, 142.3, 129.8, 129.4, 125.9, 124.6, 124.5, 121.7, 120.7, 105.6, 55.6, 13.7.
2-methoxy-9-phenylacridine (3q) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow
solid (54.1 mg, 95%): 1H NMR (400 MHz, CDCl3) δ 8.26 – 8.21 (m, 1H), 8.16 (d, J = 9.6 Hz, 1H), 7.68 (ddd, J = 7.6, 6.4, 1.2 Hz,
1H), 7.64 – 7.54 (m, 4H), 7.47 – 7.35 (m, 4H), 6.81 (d, J = 2.8 Hz, 1H), 3.71 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 156.9,
147.2, 146.0, 144.6, 136.4, 131.2, 130.3, 129.6, 128.8, 128.6, 128.3, 126.3, 126.0, 125.7, 125.4, 125.0, 102.0, 55.3.
2-methoxy-9-methylacridine (3r) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a yellow
solid (36.2 mg, 81%): 1H NMR (400 MHz, CDCl3) δ 8.19 – 8.12 (m, 2H), 8.09 (d, J = 9.2 Hz, 1H), 7.71 – 7.65 (m, 1H), 7.53 – 7.47
(m, 1H), 7.46 – 7.41 (m, 1H), 7.22 (d, J = 2.4 Hz, 1H), 3.95 (s, 3H), 2.95 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 156.8, 146.9,
145.5, 139.3, 131.8, 130.2, 128.6, 126.2, 125.7, 125.5, 124.7, 124.1, 100.0, 55.4, 13.7.
2-(tert-butyl)-9-phenylacridine (3s) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as a
yellow solid (56.0 mg, 90%): 1H NMR (400 MHz, CDCl3) δ 8.24 (dd, J = 14.8, 8.8 Hz, 2H), 7.88 (dd, J = 9.2, 2.0 Hz, 1H), 7.76 -
7.67 (m, 2H), 7.64 – 7.55 (m, 4H), 7.47 – 7.42 (m, 2H), 7.39 (ddd, J = 8.0, 6.8, 1.2 Hz, 1H), 1.31 (s, 9H). 13C{1H} NMR (101 MHz,
CDCl3) δ 148.5, 148.1, 147.8, 146.7, 136.2, 130.5, 129.6, 129.6, 129.5, 129.2, 128.4, 128.3, 126.8, 125.4, 125.3, 124.8, 120.8, 35.1,
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methyl 9-methylacridine-2-carboxylate (3t) The product was isolated by flash chromatography (EA : PE : TEA = 1 : 50 : 0.04) as
a yellow solid (39.6 mg, 78%): mp: 184-186 oC; 1H NMR (400 MHz, CDCl3) δ 8.97 (s, 1H), 8.24 (dd, J = 9.2, 2.0 Hz, 1H), 8.20 –
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