121.60, 119.98, 108.30 (2C), 42.67 (2C), 25.37. HRMS (ESI): Cacld for [M+H]+ (C17H19N3) requires m/z
265.1573, found 265.1515.
1
N1,N1-Diethyl-N3-(2-methylquinolin-4-yl)propane-1,3-diamine (3f): pale yellow liquid. H NMR (400
MHz, CDCl3): δ 7.90 (d, J = 8.4 Hz, 1H), 7.78 (s, 1H), 7.71 (d, J = 8.4 Hz, 1H), 7.57 (t, J = 8.3 Hz, 1H),
7.32 (t, J = 8.3 Hz, 1H), 6.23 (s, 1H), 3.39 (q, J = 4.1 Hz, 2H), 2.68 (t, J = 8.3 Hz, 2H), 2.64 (q, J =8.0 Hz,
13
4H), 2.61 (s, 3H), 1.95-1.88 (m, 2H), 1.10 (t, J = 7.1 Hz, 6H). C NMR (101 MHz, CDCl3): δ 159.52,
150.72, 148.13, 128.85, 128.66, 123.35, 120.36, 117.80, 98.15, 53.46, 47.02 (2C), 44.55, 25.67, 24.47,
11.57 (2C). HRMS (ESI): Cacld for [M+H]+ (C17H26N3) requires m/z 272.2121, found 272.2127.
1
N1,N1-Dimethyl-N3-(2-methylquinolin-4-yl)propane-1,3-diamine (3g): pale yellow liquid. H NMR
(400 MHz, CDCl3): δ 7.89 (d, J = 7.8 Hz, 1H), 7.64 (d, J = 7.7 Hz, 1H), 7.53 (s, 1H), 7.43 (s, 1H), 7.30 (t,
J = 4.2 Hz, 1H), 6.20 (s, 1H), 3.31 (s, 2H), 2.59 (s, 3H), 2.47 (s, 2H), 2.30 (s, 6H), 1.84 (s, 2H). 13C NMR
(101 MHz, CDCl3): δ 159.43, 150.64, 148.13, 128.79, 128.60, 123.59, 119.94, 117.81, 98.25, 59.06,
45.42 (2C), 43.58, 25.56, 24.81. HRMS (ESI): Cacld for [M+H]+ (C15H22N3) requires m/z 244.1808,
found 244.1799.
N1,N1-Dimethyl-N2-(2-methylquinolin-4-yl)ethane-1,2-diamine (3h): pale yellow liquid. 1H NMR (400
MHz, CDCl3): δ 7.90 (d, J = 8.3 Hz, 1H), 7.76 (d, J = 8.3 Hz, 1H), 7.58 (t, J = 8.3 Hz, 1H), 7.35 (t, J =
8.3 Hz, 1H), 6.28 (s, 1H), 5.84 (s, 1H), 3.28 (dd, J = 11.3, 4.9 Hz, 2H), 2.66 (t, J = 6.9 Hz, 2H), 2.61 (s,
3H), 2.29 (s, 6H). 13C NMR (101 MHz, CDCl3): δ 159.52, 149.93, 148.14, 129.02, 128.83, 123.78,
119.67, 117.56, 99.10, 57.16, 45.06 (2C), 39.95, 25.64. HRMS (ESI): Cacld for [M+H]+ (C14H20N3)
requires m/z 230.1652, found 230.1641.
1
N1-(2-Methylquinolin-4-yl)propane-1,3-diamine (3i): white solid, mp 98.7-99.2 C. H NMR (400
MHz, CDCl3): δ 7.89 (d, J = 8.4 Hz, 1H), 7.73 (d, J = 8.3 Hz, 1H), 7.57 (t, J = 7.6 Hz, 1H), 7.33 (t, J =
7.5 Hz, 1H), 6.78 (s, 1H), 6.28 (s, 1H), 3.44-3.38 (m, 2H), 3.02 (t, J = 5.8 Hz, 2H), 2.60 (s, 3H), 1.94-1.86
13
(m, 3H). C NMR (101 MHz, DMSO-d6): δ 159.15, 150.48, 148.51, 129.05, 128.76, 123.40, 121.87,
117.97, 98.38, 41.06, 39.93, 31.42, 25.74. HRMS (ESI): Cacld for [M+H]+ (C13H18N3) requires m/z
216.1495, found 216.1485.
N,N-Diethyl-2-methylquinolin-4-amine (3j): pale yellow liquid. 1H NMR (400 MHz, CDCl3): δ 8.04 (d,
J = 8.4 Hz, 1H), 7.99 (d, J = 8.3 Hz, 1H), 7.62 (t, J = 7.2 Hz, 1H), 7.41 (t, J = 7.6 Hz, 1H), 6.70 (s, 1H),
13
3.40 (q, J = 7.1 Hz, 4H), 2.70 (s, 3H), 1.20 (t, J = 7.1 Hz, 6H). C NMR (101 MHz, CDCl3): δ 158.04,
156.33, 148.27, 129.41, 127.96, 124.26, 124.11, 122.40, 110.04, 46.40 (2C), 24.86, 12.21 (2C). HRMS
(ESI): Cacld for [M+H]+ (C14H19N2) requires m/z 215.1543, found 215.1533.
1
2-Methyl-N-propylquinolin-4-amine (3k): white solid, mp 102.7-103.9 C. H NMR (400 MHz,
CDCl3): δ 7.90 (d, J = 8.4 Hz, 1H), 7.69 (d, J = 8.2 Hz, 1H), 7.56 (t, J = 7.6 Hz, 1H), 7.31 (t, J = 7.5 Hz,