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Organic & Biomolecular Chemistry
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ARTICLE
Journal Name
J = 8 Hz, CH2), 2.81 (2H, q, J = 7.5 Hz, CH2), 1.81 (2H, sext, J = 7.4 7.68 (1H, dd, J = 8.9, 6.1 Hz, H-5), 7.61 (1H, dd, J = 10.4, 2.4 Hz,
Hz, CH2), 1.33 (3H, t, J = 7.5 Hz, CH3), 1.06 (3H, t, J = 7.3 Hz, CH3); H-8), 7.20 (1H, td, J = 8.6, 2.5 Hz, H-6), 2.91 (2H,Vtie,wJA=rtic7le.5OnHlinze,
DOI: 10.1039/C9OB02214G
13C NMR δC (100 MHz; CDCl3; Me4Si) 159.6, 157.4, 142.6, 135.8, CH2), 2.79 (2H, q, J = 7.5 Hz, CH2), 1.78 (2H, sext, J = 7.5 Hz, CH2),
133.2, 130.0, 128.4, 121.0, 104.9, 55.7, 37.7, 25.4, 23.2, 14.7, 1.30 (3H, t, J = 7.5 Hz, CH3), 1.03 (3H, t, J = 7.3 Hz, CH3); 19F NMR
δF (377 MHz; CDCl3) -116.83 (1F, s, F-7); 13C NMR δC (150 MHz;
CDCl3; Me4Si) 163.5, 163.4, 161.8, 147.4, 147.3, 134.9, 134.9,
134.0, 129.0, 128.9, 124.5, 116.2, 116.0, 112.4, 112.2, 77.4,
14.5; IR (KBr) νmax/cm1 2961(C-H), 1623 (C=C),1224 (C-O); HRMS
(ESI) Calcd For C15H20NO 230.1545 (M + H+); Found 230.1560.
3-ethyl-2-propylquinoline (3b): (153 mg, 77%, brown liquid); 1H
NMR δH (600 MHz; CDCl3; Me4Si) 7.99 (1H, d, J = 8.4 Hz, H-8), 77.2, 77.2, 37.9, 25.3, 23.0, 14.6, 14.6.; IR (KBr) νmax/cm1 2963
7.83 (1H s, H-4), 7.70 (1H, d, J = 8.0 Hz, H-5), 7.58 (1H, t, J = 7.4 (C-H), 1627 (C=C); HRMS (ESI) Calcd For C14H17FN 218.1345 (M
Hz, H-7), 7.41 (1H, t, J = 7.4 Hz, H-6), 2.93 (2H, t, J = 7.3 Hz, CH2), + H+); Found 218.1364.
2.81 (2H, q, J = 7.5 Hz, CH2), 1.80 (2H, sext, J = 7.5 Hz, CH2), 1.31 3-ethyl-8-methoxy-2-propylquinoline (3h): (162 mg, 71%, dark
(3H, t, J = 7.5 Hz, CH3), 1.04 (3H, t, J = 7.3 Hz, CH3); 13C NMR δC brown liquid); 1H NMR δH (600 MHz; CDCl3; Me4Si) 7.85 (1H, s,
(150 MHz; CDCl3; Me4Si) 162.2, 146.5, 135.5, 134.1, 128.6, H-4), 7.37 (1H, t, J = 7.9 Hz, H-6), 7.32 (1H, d, J = 7.9 Hz, H-5),
128.5, 127.5, 127.1, 125.7, 38.0, 25.3, 23.1, 14.6, 14.6; IR (KBr) 6.98 (1H, d, J = 7.6 Hz, H-7), 4.08 (3H, s, 8-OCH3), 3.02 (2H, t, J =
νmax/cm1 2978 (C-H), 1630 (C=C); HRMS (ESI) Calcd For C14H18N
7.5 Hz, CH2), 2.86 (2H, q, J = 7.5 Hz, CH2), 1.84 (2H, sext, J = 7.5
Hz, CH2), 1.35 (3H, t, J = 7.5 Hz, CH3), 1.07 (3H, t, J = 7.3 Hz, CH3);
13C NMR δC (150 MHz; CDCl3; Me4Si) 161.3, 155.1, 138.4, 136.0,
134.1, 128.7, 125.7, 119.1, 106.9, 56.2, 38.2, 25.3, 23.4, 14.6,
200.1439 (M + H+); Found 200.1472.
3,6-diethyl-2-propylquinoline (3c): (188 mg, 83%, brown
liquid); 1H NMR δH (600 MHz; CDCl3; Me4Si) 7.91 (1H, d, J = 8.6
Hz, H-8), 7.78 (1H, s, H-4), 7.47 (1H, d, J = 1.9 Hz H-5), 7.45 (1H, 14.6; IR (KBr) νmax/cm1 2960 (C-H), 1623 (C=C), 1262 (C-O);
dd, J = 8.6, 1.9 Hz, H-7), 2.91 (2H, t, J = 7.4 Hz, CH2), 2.78 (4H,dq, HRMS (ESI) Calcd For C15H20NO 230.1545 (M + H+); Found
J = 12.0, 7.5 Hz, 2CH2), 1.78 (2H, dq, J = 15.1, 7.4 Hz, CH2), 1.29 230.1557.
(6H, m, 2CH3), 1.03 (3H, t, J = 7.3 Hz, CH3); 13C NMR δC (150 MHz; 3-ethyl-8-methyl-2-propylquinoline (3i): (160 mg, 75%, yellow
1
CDCl3; Me4Si) 161.3, 145.2, 141.8, 135.5, 133.8, 129.8, 128.3, liquid); H NMR δH (600 MHz; CDCl3; Me4Si) 7.77 (1H, s, H-4),
127.6, 124.7, 37.9, 29.0, 25.4, 23.2, 15.7, 14.6, 14.5; IR (KBr) 7.54 (1H, d, J = 8.1 Hz, H-5), 7.42 (1H, d, J = 6.9 Hz, H-7), 7.30
νmax/cm1 2963 (C-H), ,1634 (C=C); HRMS (ESI) Calcd For C16H22N
(1H, t, J = 8.1 Hz, H-6), 2.92 (2H, t, J = 7.5 Hz, CH2), 2.81 – 2.77
(2H, m, CH2), 2.76 (3H, s, 8-CH3), 1.91 (2H, sext, J = 7.5 Hz, CH2),
1.30 (3H, t, J = 7.5 Hz, CH3), 1.05 (3H, t, J = 7.4 Hz, CH3); 13C NMR
δC (150 MHz; CDCl3; Me4Si) 160.5, 145.5, 136.8, 135.2, 133.9,
128.4, 127.3, 125.4, 125.0, 37.6, 25.3, 22.0, 18.0, 14.6, 14.5; IR
(KBr) νmax/cm1 2963 (C-H), 1635 (C=C); HRMS (ESI) Calcd For
C15H20N 214.1596 (M + H+); Found 214.1619.
228.1752 (M + H+); Found 228.1765.
3-ethyl-6-fluoro-2-propylquinoline (3d): (128 mg, 59%, brown
liquid); 1H NMR δH (600 MHz; CDCl3; Me4Si) 7.99 (1H, dd, J = 9.1,
5.3 Hz, H-8), 7.80 (1H, s, H-4), 7.37 (1H, dd, J = 8.8, 2.8 Hz, H-5),
7.34 (1H, dd, J = 9.0, 2.8 Hz, H-7), 2.94 (2H, t, J = 7.5 Hz, CH2),
2.83 (2H, q, J = 7.5 Hz, CH2), 1.82 (2H, sext, 7.4 Hz, CH2), 1.34
(3H, t, J = 7.5 Hz, CH3), 1.07 (3H, t, J = 7.4 Hz, CH3); 19F NMR δF
(377 MHz; CDCl3; Me4Si) -115.34 (1F, s, F-6); 13C NMR δC (150
MHz; CDCl3; Me4Si) 161.5, 161.5, 161.0, 159.3, 143.6, 136.4,
133.4, 133.4, 131.0, 130.9, 128.0, 127.9, 118.6, 118.4, 110.1,
109.9, 37.8, 25.3, 23.0, 14.6, 14.5; IR (KBr) νmax/cm1 2963 (C-H),
1628 (C=C); HRMS (ESI) Calcd For C14H17FN 218.1345 (M + H+);
Found 218.1370.
3-ethyl-6,7-dimethoxy-2-propylquinoline (3j): (218 mg, 84%,
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brown liquid); H NMR δH (400 MHz; CDCl3; Me4Si) 7.72 (1H, s,
H-4), 7.37 (1H, s, H-8), 6.98 (1H, s, H-5), 4.00 (3H, s, 7-OCH3),
3.98 (3H, s, 6-OCH3), 2.90 (2H, t, J = 7.5 Hz, CH2), 2.79 (2H, q, J =
7.5 Hz, CH2), 1.79 (2H, sext, J = 7.5 Hz, CH2), 1.31 (3H, t, J = 7.5
Hz, CH3), 1.05 (3H, t, J = 7.3 Hz, CH3); 13C NMR δC (100 MHz;
CDCl3; Me4Si) 159.4, 151.5, 149.0, 143.0, 133.4, 132.7, 122.5,
107.2, 104.6, 56.0, 55.9, 37.5, 25.0, 23.1, 14.7, 14.3;IR (KBr)
νmax/cm1 2961 (C-H), 1623 (C=C), 1267 (C-O); HRMS (ESI) Calcd
For C16H22NO2 260.1651 (M + H+); Found 260.1611.
3-ethyl-7-methoxy-2-propylquinoline (3e): (158 mg, 69%, dark
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brown liquid); H NMR δH (600 MHz; CDCl3; Me4Si) 7.76 (1H, s,
3-ethyl-6,7-dimethyl-2-propylquinoline (3k): (188 mg, 83%,
yellow solid); mp 72-73˚C; 1H NMR δH (400 MHz; CDCl3; Me4Si)
7.71 (1H, s, H-4), 7.67 (1H, s, H-8), 7.38 (1H, s, H-5), 2.85 (2H, t,
J = 7.5 Hz, CH2), 2.73 (2H, q, J = 7.5 Hz, CH2), 2.36 (3H, s, 7-CH3),
2.33 (3H, s, 6-CH3), 1.74 (2H, sext, J = 7.5 Hz, CH2), 1.24 (3H, t, J
= 7.5 Hz, CH3), 0.98 (3H, t, J = 7.3 Hz, CH3); 13C NMR δC (100 MHz;
CDCl3; Me4Si) 161.1, 145.7, 138.5, 135.4, 134.6, 133.2, 128.0,
126.3, 126.1, 37.9, 25.4, 23.2, 20.5, 20.1, 14.7, 14.5; IR (KBr)
νmax/cm1 2942 (C-H), 1646 (C=C); HRMS (ESI) Calcd For C16H22N
228.1752 (M + H+); Found 228.1775.
3-ethyl-6,8-dimethoxy-2-propylquinoline (3l): (207 mg, 80%,
dark brown liquid); 1H NMR δH (400 MHz; CDCl3; Me4Si) 7.66 (1H,
s, H-4), 6.56 (1H, s, H-5), 6.53 (1H, s, H-7), 3.95 (3H, s, 8-OCH3),
3.83 (3H, s, 6-OCH3), 2.89 (2H, t, J = 7.5 Hz, CH2), 2.74 (2H, q, J =
7.5 Hz, CH2), 1.74 (2H, sext, J = 7.5 Hz, CH2), 1.25 (3H, t, J = 7.5
Hz, CH3), 0.97 (3H, t, J = 7.3 Hz, CH3); 13C NMR δC (100 MHz;
CDCl3; Me4Si) 158.4, 157.4, 155.9, 136.3, 134.9, 133.1, 128.9,
100.1, 96.4, 56.1, 55.4, 37.7, 25.1, 23.1, 14.5, 14.4; IR (KBr)
νmax/cm1 2959 (C-H), 1621 (C=C), 1260 (C-O); HRMS (ESI) Calcd
For C16H22NO2 260.1651 (M + H+); Found 260.1661.
H-4), 7.58 (1H, d, J = 8.9 Hz, H-5), 7.33 (1H, d, J = 2.4 Hz, H-8),
7.07 (1H, dd, J = 8.9, 2.5 Hz, H-6), 3.90 (3H, s, OCH3), 2.91 (2H, t,
J = 7.5 Hz, CH2), 2.77 (2H, q, J = 7.5 Hz, CH2), 1.78 (2H, sext, J =
7.5 Hz, CH2), 1.29 (3H, t, J = 7.5 Hz, CH3), 1.03 (3H, t, J = 7.3 Hz,
CH3); 13C NMR δC (150 MHz; CDCl3; Me4Si) 162.4, 160.1, 148.0,
134.1, 133.2, 128.1, 122.7, 118.8, 106.6, 55.7, 38.0, 25.2, 23.4,
14.8, 14.6; IR (KBr) νmax/cm1 2957 (C-H), 1621 (C=C), 1215 (C-
O); HRMS (ESI) Calcd For C15H20NO 230.1545 (M + H+); Found
230.1565.
3-ethyl-7-methyl-2-propylquinoline (3f): (168 mg, 79%, brown
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liquid); H NMR δH (600 MHz; CDCl3; Me4Si) 7.78 (1H, s, H-4),
7.77 (1H, s, H-8), 7.59 (1H, d, J = 8.2 Hz, H-5), 7.25 (1H, dd, J =
8.2, 1.4 Hz, H-6), 2.91 (2H, t, J = 7.5 Hz, CH2), 2.79 (2H, q, J = 7.5
Hz, CH2), 2.50 (3H, s, 7-CH3), 1.78 (2H, sext, J = 7.5 Hz, CH2), 1.30
(3H, t, J = 7.5 Hz, CH3), 1.03 (3H, t, J = 7.3 Hz, CH3); 13C NMR δC
(150 MHz; CDCl3; Me4Si) 162.1, 146.7, 138.6, 134.6, 133.9,
127.9, 127.6, 126.7, 125.5, 37.9, 25.3, 23.1, 22.0, 14.7, 14.6; IR
(KBr) νmax/cm1 2958 (C-H), 1623 (C=C), 1226 (C-O); HRMS (ESI)
Calcd For C15H20N 214.1596 (M + H+); Found 214.1613.
3-ethyl-7-fluoro-2-propylquinoline (3g): (119 mg, 55%, brown
liquid); 1H NMR δH (600 MHz; CDCl3; Me4Si) δ 7.82 (1H, s, H-4),
6 | J. Name., 2012, 00, 1-3
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