830
Rádl, Obadalová:
337.6 (4.16), 324.4 (4.11), 238.0 (4.25), 212.0 (4.41). 1H NMR (CDCl3): 3.79 s, 3 H (CH3);
6.25 d, J = 7.7, 1 H (H-3); 7.38 m , 1 H (arom . H); 7.40 m , 1 H (arom . H); 7.50 d, J = 7.7, 1 H
(H-2); 7.68 m , 1 H (arom . H); 8.45 m , 1 H (H-5).
1-Ethyl-1,4-dihydroquinolin-4-one (5b). Yields 76% (m eth od A) an d 74% (m eth od C); m .p.
101–103 °C (h exan e) (lit.23, 100–102 °C; lit.22a, 102–103 °C). For C11H11NO (173.2) calcu-
lated: 76.28% C, 6.40% H, 8.09% N; foun d: 75.86% C, 6.47% H, 7.89% N. IR: 1620.6 (C=O).
UV (eth an ol), λm ax (log ε): 338.0 (4.19), 324.8 (4.15), 237.8 (4.30), 213.0 (4.43). 1H NMR
(CDCl3): 1.47 t, J = 7.2, 3 H (CH3); 4.16 q, J = 7.2, 2 H (CH2); 6.24 d, J = 7.7, 1 H (H-3);
7.35 m , 1 H (arom . H); 7.43 d, J = 8.5, 1 H (H-8); 7.54 d, J = 7.8, 1 H (H-2); 7.65 m , 1 H
(arom . H); 8.45 dd, J = 8.1, 0.5, 1 H (H-5).
1-Cyclopropyl-1,4-dihydroquinolin-4-one (5c). Yields 61% (m eth od A) an d 57% (m eth od B);
m .p. 85–88 °C (cycloh exan e). For C12H11NO (185.3) calculated: 77.81% C, 5.99% H, 7.56% N;
foun d: 77.57% C, 6.12% H, 7.73% N. IR: 1613.4 (C=O). UV (eth an ol), λm ax (log ε): 336.6
(4.20), 3234.4 (4.14), 238.4 (4.28), 212.8 (4.39). 1H NMR (CDCl3): 1.06 m , 2 H (CH2);
1.28 m , 2 H (CH2); 3.39 m , 1 H (cyclopropyl CH); 6.22 d, J = 7.8, 1 H (H-3); 7.39 m , 1 H
(arom . H); 7.68 m , 1 H (arom . H); 7.68 d, J = 7.8, 1 H (H-2); 7.91 ddd, J = 8.6, 1.0, 0.6, 1 H
(H-8); 8.42 ddd, J = 8.1, 1.7, 0.5, 1 H (H-5).
1-Phenyl-1,4-dihydroquinolin-4-one (5e). Yields 66% (m eth od A) an d 68% (m eth od C); m .p.
118–123 °C (eth yl acetate). For C15H11NO (221.3) calculated: 81.43% C, 5.01% H, 6.33% N;
foun d: 81.22% C, 5.29% H, 6.01% N. IR: 1628.7 (C=O). UV (eth an ol), λm ax (log ε): 335.8
(4.25), 323.4 (4.20), 239.0 (4.31), 209.0 (4.85). 1H NMR (CDCl3): 6.37 d, J = 7.8, 1 H (H-3);
7.00 ddd, J = 8.5, 1.1, 0.5, 1 H (H-8); 7.60 d, J = 7.8, 1 H (H-2); 7.32–7.65 m , 7 H (arom . H);
8.47 ddd, J = 8.0, 1.7, 0.5, 1 H (H-5).
1,2-Dimethyl-1,4-dihydroquinolin-4-one (5f). Yields 81% (m eth od A) an d 83% (m eth od B);
m .p. 176–178 °C (toluen e) (lit.24a, 174–175 °C; lit.10b, 175 °C; lit.24b, 177.5–178 °C). For
C
11H11NO (173.2) calculated: 76.28% C, 6.40% H, 8.09% N; foun d: 76.11% C, 6.13% H,
8.24% N. IR: 1595.3 (C=O). UV (eth an ol), λm ax (log ε): 335.4 (4.14), 322.2 (4.12), 239.4
(4.38), 211.8 (4.47). 1H NMR (CDCl3): 2.42 d, J = 0.4, 3 H (CH3); 3.68 s, 3 H (N-CH3); 6.16 d,
J = 0.4, 1 H (H-3); 7.34 m , 1 H (H-6); 7.44 d, J = 8.5, 1 H (H-8); 7.62 m , 1 H (H-7); 8.41 ddd,
J = 8.0, 1.7, 0.4, 1 H (H-5).
1-Ethyl-2-methyl-1,4-dihydroquinolin-4-one (5g). Yield 80% (m eth od B); m .p. 116–118 °C
(eth yl acetate). For C12H13NO (187.2) calculated: 76.98% C, 7.00% H, 7.48% N; foun d:
76.54% C, 6.83% H, 7.66% N. IR: 1595.3 (C=O). UV (eth an ol), λm ax (log ε): 335.0 (4.15),
321.8 (4.17), 239.2 (4.37), 210.0 (4.67). 1H NMR (CDCl3): 1.43 t, J = 7.2, 3 H (eth yl CH3);
2.48 s, 3 H (CH3); 4.22 q, J = 7.2, 2 H (CH2); 6.21 s, 1 H (H-3); 7.35 m , 1 H (H-6); 7.49 d, J =
8.7, 1 H (H-8); 7.65 m , 1 H (H-7); 8.45 dd, J = 8.0, 1.7, 1 H (H-5).
1-Cyclopropyl-2-methyl-1,4-dihydroquinolin-4-one (5h ). Yield 85% (m eth od B); m .p. 164–
168 °C (eth yl acetate). For C13H13NO (199.3) calculated: 78.36% C, 6.58% H, 7.03% N;
foun d: 78.05% C, 6.37% H, 7.29% N. IR: 1595.3 (C=O). UV (eth an ol), λm ax (log ε): 333.8
(4.16), 321.8 (4.13), 239.2 (4.39), 215.2 (4.32). 1H NMR (CDCl3): 0.96 m , 2 H (CH2); 1.39 m ,
2 H (CH2); 2.57 d, J = 0.6, 3 H (CH3); 3.21 m , 1 H (cyclopropyl CH); 6.16 d, J = 0.6, 1 H
(H-3); 7.31 m , 1 H (H-6); 7.59 m , 1 H (H-7); 7.87 ddd, J = 8.7, 1.0, 0.5, 1 H (H-8); 8.36 ddd,
J = 8.0, 1.7, 0.5, 1 H (H-5).
2-Methyl-1-phenyl-1,4-dihydroquinolin-4-one (5j). Yield 72% (m eth od A); m .p. 265–267 °C
(eth yl acetate). For C16H13NO (235.3) calculated: 81.68% C, 5.57% H, 5.95% N; foun d:
81.19% C, 5.33% H, 6.29% N. IR: 1622.7 (C=O). UV (eth an ol), λm ax (log ε): 332.6 (4.22),
320.0 (4.19), 238.8 (4.38), 209.0 (4.49). 1H NMR (CDCl3): 2.07 s, 3 H (CH3); 6.33 s, 1 H
Collect. Czech. Chem. Commun. (Vol. 69) (2004)