SYNTHESIS OF 4,N-DIARYL-2-METHYL-5-OXO-1,4,5,6,7,8-HEXAHYDROQUINOLINE-...
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The H NMR spectra were measured on a Bruker
Yield 2.5 g (62%), mp 120–122°C. IR spectrum, ν,
cm–1: 3288 (NH), 1678 (C=O, amide), 1634 (C5=O).
1H NMR spectrum, δ, ppm: 1.72–1.86 m (2H, 7-H),
1.87–1.92 m (2H, 8-H), 2.08 s (3H, CH3), 2.11–2.33 m
(2H, 6-H), 5.15 s (1H, 4-H), 6.97–8.10 m (9H, C6H5,
C6H4), 8.97 s (1H, NH), 9.65 s (1H, NH). Found, %:
C 68.30; H 5.07; N 10.65. C23H21N3O4. Calculated, %:
C 68.47; H 5.25; N 10.47.
DRX-500 instrument at 500.13 MHz using DMSO-d6
as solvent and tetramethylsilane as internal reference.
The mass spectra (electron impact, 70 eV) were ob-
tained on a Finnigan MAT INCOS-50 mass spec-
trometer.
2-Methyl-5-oxo-4,N-diphenyl-1,4,5,6,7,8-hexa-
hydroquinoline-3-carboxamide (Ia). A mixture of
1.12 g (0.01 mol) of cyclohexane-1,3-dione, 1.06 ml
(0.01 mol) of benzaldehyde, 1.70 g (0.01 mol) of
acetoacetanilide, and 0.77 g (0.01 mol) of ammonium
acetate was heated for 10–20 min at 150–160°C until
gaseous products no longer evolved and the mixture
solidified. The resulting material was cooled and
treated with ethanol, and the precipitate was filtered
off and recrystallized from ethanol. Yield 2.5 g (69%),
mp 250–252°C. IR spectrum, ν, cm–1: 3200 (NH),
2-Methyl-N-(2-methylphenyl)-5-oxo-4-phenyl-
1,4,5,6,7,8-hexahydroquinoline-3-carboxamide (Ie).
Yield 2.3 g (62%), mp 188–190°C. IR spectrum, ν,
cm–1: 3228 (NH), 1675 (C=O, amide), 1633 (C5=O).
1H NMR spectrum, δ, ppm: 1.72–1.82 m (2H, 7-H),
1.87–1.95 m (2H, 8-H), 2.06 s (3H, CH3), 2.11–2.32 m
(2H, 6-H), 2.32 s (3H, CH3C6H4), 4.95 s (1H, 4-H),
6.77–7.25 m (9H, C6H5, C6H4), 8.57 s (1H, NH), 8.85 s
(1H, NH). Found, %: C 77.20; H 6.71; N 7.25.
C24H24N2O3. Calculated, %: C 77.39; H 6.49; N 7.52.
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1664 (C=O, amide), 1632 (C5=O). H NMR spectrum,
δ, ppm: 1.75–1.82 m (2H, 7-H), 1.87–1.95 m (2H,
8-H), 2.03 s (3H, CH3), 2.15–2.26 m (2H, 6-H), 4.99 s
(1H, 4-H), 6.97–7.56 m (10H, C6H5), 8.75 s (1H, NH),
9.53 s (1H, NH). Found, %: C 76.86; H 6.00; N 7.87.
C23H22N2O2. Calculated, %: C 77.07; H 6.19; N 7.82.
4-(4-Chlorophenyl)-2-methyl-N-(2-methyl-
phenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-
carboxamide (If). Yield 2.0 g (50%), mp 243–245°C.
IR spectrum, ν, cm–1: 3236 (NH), 1670 (C=O, amide),
1624 (C5=O). 1H NMR spectrum, δ, ppm: 1.73–1.84 m
(2H, 7-H), 1.86–1.95 m (2H, 8-H), 2.03 s (3H, CH3),
2.11–2.30 m (2H, 6-H), 2.32 s (3H, CH3C6H4), 4.91 s
(1H, 4-H), 6.67–7.31 m (8H, C6H4, C6H4), 8.53 s (1H,
NH), 8.75 s (1H, NH). Mass spectrum, m/z (Irel, %):
406 (33) [M – H]+, 299 (100), 281 (3). Found, %:
C 70.40; H 5.87; N 6.65. C24H24ClN2O2. Calculated,
%: C 70.67; H 5.93; N 6.87. M 406.
Compounds Ib–Ii were synthesized in a similar
way.
4-(4-Chlorophenyl)-2-methyl-5-oxo-N-phenyl-
1,4,5,6,7,8-hexahydroquinoline-3-carboxamide (Ib).
Yield 2.1 g (53%), mp 243–245°C. IR spectrum, ν,
cm–1: 3208 (NH), 1663 (C=O, amide), 1632 (C5=O).
1H NMR spectrum, δ, ppm: 1.73–1.85 m (2H, 7-H),
1.91–1.96 m (2H, 8-H), 2.02 s (3H, CH3), 2.11–2.32 m
(2H, 6-H), 4.96 s (1H, 4-H), 6.98–7.53 m (9H, C6H5,
C6H4), 8.81 s (1H, NH), 9.58 s (1H, NH). Mass spec-
trum, m/z (Irel, %): 392 (36) [M – H]+, 300 (100) [M –
NHPh]+, 281 (83) [M – PhNH]+, 272 (16) [M –
CONHPh]+. Found, %: C 70.01; H 5.69; N 7.05.
C23H21ClN2O2. Calculated, %: C 70.31; H 5.93;
N 7.13. M 392.
2-Methyl-N-(2-methylphenyl)-4-(3-nitrophenyl)-
5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbox-
amide (Ig). Yield 3.5 g (85%), mp 165–167°C. IR
spectrum, ν, cm–1: 3238 (NH), 1675 (C=O, amide),
1634 (C5=O). 1H NMR spectrum, δ, ppm: 1.72–1.84 m
(2H, 7-H), 1.85–1.95 m (2H, 8-H), 2.03 s (3H, CH3),
2.11–2.30 m (2H, 6-H), 2.32 s (3H, CH3C6H4), 4.81 s
(1H, 4-H), 6.53–7.25 m (8H, C6H4), 8.43 s (1H, NH),
8.75 s (1H, NH). Found, %: C 68.80; H 5.27; N 9.95.
C24H23N3O4. Calculated, %: C 69.07; H 5.55; N 10.07.
M 417.
2-Methyl-4-(4-nitrophenyl)-5-oxo-N-phenyl-
1,4,5,6,7,8-hexahydroquinoline-3-carboxamide (Ic).
Yield 2.7 g (67%), mp 239–241°C. IR spectrum, ν,
cm–1: 3208 (NH), 1672 (C=O, amide), 1632 (C5=O).
1H NMR spectrum, δ, ppm: 1.71–1.82 m (2H, 7-H),
1.87–1.96 m (2H, 8-H), 2.06 s (3H, CH3), 2.11–2.32 m
(2H, 6-H), 5.10 s (1H, 4-H), 6.95–8.13 m (9H, C6H5,
C6H4), 8.92 s (1H, NH), 9.72 s (1H, NH). Found, %:
C 68.30; H 5.07; N 10.65. C23H21N3O4. Calculated, %:
C 68.47; H 5.25; N 10.47.
2-Methyl-N-(2-methylphenyl)-4-(4-nitrophenyl)-
5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbox-
amide (Ih). Yield 2.8 g (68%), mp 178–180°C. IR
spectrum, ν, cm–1: 3288 (NH), 1638 (C=O, amide),
1631 (C5=O). 1H NMR spectrum, δ, ppm: 1.73–1.85 m
(2H, 7-H), 1.86–1.97 m (2H, 8-H), 2.07 s (3H, CH3),
2.13–2.30 m (2H, 6-H), 2.33 s (3H, CH3C6H4), 5.11 s
(1H, 4-H), 6.77–7.98 m (8H, C6H4), 8.63 s (1H, NH),
2-Methyl-4-(3-nitrophenyl)-5-oxo-N-phenyl-
1,4,5,6,7,8-hexahydroquinoline-3-carboxamide (Id).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 6 2011