J Fluoresc
sample was put in a quartz cuvette and it was mounted on the
sample holder.
CH, J: 9.2, 8.0 Hz), 13C NMR (100 MHz, CDCl3): 21.3 (CH3),
55.5 (OCH3), 103.7 (Ar. CH), 115.7 (Ar. CH), 118.5 (Ar. CH),
120.3 (Ar. CH), 122.1 (Ar. CH), 123.5 (Ar. CH), 126.6 (ar. CH),
127.1 (Ar. CH), 129.6 (Ar. CH), 130.6 (Ar. CH), 131.6 (Ar.
CH), 136.7 (Ar. CH), 139.1 (Ar. CH), 143.8 (Ar. CH), 144.9
(Ar. CH), 145.1 (Ar. CH), 155.0 (Ar. CH), 157.8 (Ar. CH), ESI-
MS: [M + H]+ m/z: 341; Chemical Formula: C23H20N2O.
General Procedure for the Preparation of 4a-f
An equimolar mixture of aromatic amines 1 (1.0 mmol) and
aromatic aldehydes 2 (1.0 mmol) in presence of 10 mol% of
InCl3 were refluxed in 5 mL of toluene. Then after refluxing
for 1 h (as indicated by TLC), 2-ethynylaniline 3 (1.0 mmol)
was added to reaction pot and refluxed the system for another
23 h. Then, the completions of the reactions were monitored
by UV-lamp (giving distinct blue/green colouration). The re-
action mixture was brought to room temperature and extracted
with ethylacetate (2 × 10 mL). The organic layer containing
the quinoline was dried over anhydrous Na2SO4 and then
evaporated. The crude residue was purified by column chro-
matography over silica gel using ethyl acetate/petroleum ether
(1:5) as eluent to afford pure product 4a-i in good yields.
3. 2-(2-(4-Chlorophenyl)-6-Methoxyquinolin-4-Yl)Aniline
(4c): The crude substance purified by gravity column
chromatography (ethyl acetate/n-hexane 1:2).
Brown solid substance, yield 0.26 g (74%), m.p. 174-
176 °C, Rf: 0.70 (SiO2, ethyl acetate/n-hexane 1:2). FTIR Ѵ:
3382 (NH2), 3035, 2809, 2859 (Aromatic = CH), 1900, 1615,
1515 (C=C), 1082, 815,600 (mono-substituted aromatic ring
1
C-Cl), H NMR (400 MHz, CHCl3-d): δ (ppm): 3.80(s, 3H,
CH3), 6.87(d, 1H, Ar. =CH, J: 5.2 Hz), 6.96–6.1(m, 2H, Ar.
=CH), 7.21–7.19 (m, 1H, Ar. =CH), 8.13–8.08 (m, 3H, Ar. =
CH), 7.33–7.30(m, 1H, Ar. =CH), 7.41–7.39(m, 1H, Ar.
=CH), 7.47(d, 2H, Ar. = CH, J: 6 Hz, 2H), 7.80(s, 1H, Ar.
=CH), 13C NMR(400 MHZ,CDCl3): 55.5 (OCH3), 103.7 (Ar.
CH), 113.6 (Ar. CH), 113.7 (Ar. CH), 118.5 (Ar. CH), 120.06
(Ar. CH), 122.46 (Ar. CH), 126.8 (Ar. CH), 128.5 (Ar. CH),
128.9 (Ar. CH), 129.7 (Ar. CH), 130.5 (Ar. CH), 131.6 (Ar.
CH), 133.2 (Ar. CH), 135.2 (Ar. CH), 137.9 (Ar. CH), 143.7
(Ar. CH), 145.4 (Ar. CH), 158.1 (Ar. CH), ESI-MS: [M + H]+
m/z 361; Chemical Formula: C22H17ClN2O.
Characterization Data of the Isolated Compounds 4a-I
1. 2-(2-Phenylquinolin-4-Yl)Aniline (4a): The crude sub-
stance purified by gravity column chromatography(ethyl
acetate/n-hexane 1:2).
White solid, yield 0.21 g (70%), m.p. 173-175 °C; Rf: 0.70
(SiO2, ethyl acetate/n-hexane 1:2), FTIR V: 3389, 3020(N-H);
2929, 2854(aromatic = C-H stretching); 1903, 1614(aromat-
ic = C-H bending), 1519(C=C); 1093, 806 (mono-substituted
1
ring C-H) cm−1, H NMR (400 MHz, CHCl3-d): δ (ppm):
4. 2-(2-(4-Bromophenyl)-6-Methoxyquinolin-4-Yl)Aniline
(4d): The crude substance purified by gravity column
chromatography (ethyl acetate/n-hexane 1:2).
3.59 (s, 2H, NH2), 6.93–6.85 (m, 3H. Ar. =CH), 7.04–7.00
(m, 2H, Ar. = CH), 7.21–7.19 (m, 1H, Ar. =CH), 7.0–7.04(d,
2H, Ar. =CH, J: 6.4 Hz), 8.12 (d, 3H, J: 7.2 Hz), 13C NMR
(100 MHz, CHCl3-d) δ (ppm): 103.7 (Ar. CH), 114.2 (Ar,
CH), 115.7 (Ar, CH), 118.5 (Ar. CH), 120.0 (Ar. CH),
122.1(Ar. CH), 123.6 (Ar. CH), 126.4(Ar. CH), 128.6 (Ar.
CH), 129.6 (Ar. CH), 130.6 (Ar. CH), 131.4 (Ar. CH),
132.2 (Ar. CH), 138.8 (Ar. CH), 144.8 (Ar. CH), 145.1 (Ar.
CH), 154.6 (Ar. CH), 157.8 (Ar. CH), ESI-MS: [M + H]+ m/z:
297; Chemical Formula: C21H16N2.
Brown solid substance, yield 0.30 g (75%) m.p. 108-
110 °C, Rf: 0.70 (SiO2, ethyl acetate/n-hexane 1:2). FTIR Ѵ:
3435 (NH2), 3318, 3205, 3063, 2916 (aromatic = C-H), 2354,
1917, 1626, 1583 (C=C), 1492, 1305, 1091, 1014, 823
(mono-substituted aromatic ring CH) cm−1,1H NMR
(400 MHz, CHCl3-d): δ (ppm): 3.81(s, 1H, OCH3), 6.99–
6.88(m, 3H, Ar. -CH), 7.35–7.19(m, 2H, Ar. =CH), 7.51–
7.41(m, 3H, Ar. =CH), 7.74(s, 1H, Ar. =CH), 8.14(d, 2H,
Ar. =CH, J: 8.4 Hz), 8.37(s,1H, Ar. =CH), 13C NMR
(100 MHz, CHCl3-d) δ (ppm): 55.3 (OCH3), 103.61 (Ar.
CH), 115.7 (Ar. CH), 118.6 (Ar. CH), 120.0 (Ar. CH),
122.5 (Ar. CH), 123.3 (Ar. CH), 123.6 (Ar. CH), 126.9 (Ar.
CH), 128.8 (Ar. CH), 129.7 (Ar. CH), 130.5 (Ar. CH), 131.6
(Ar. CH), 131.9 (Ar. CH), 143.7 (Ar. CH), 145.5 (ar. CH),
144.8 (Ar. CH), ESI-MS: [M + H]+ m/z: 405; Chemical
Formula: C22H17BrN2O.
2. 2-(6-Methoxy-2-(p-Tolyl)Quinolin-4-Yl)Aniline (4b):
The crude substance purified by gravity column
chromatography(ethyl acetate/n-hexane 1:2).
White solid, yield 0.24 g (73%), m.p. 156-158 °C; Rf: 0.70
(SiO2, ethyl acetate/n-hexane 1:2), FTIR V: 3375, 3025(N-H),
2909, 2867 (aromatic = C-H), 1903, 1617 (aromatic = C-H),
1
1511 (C=C), 1097, 810 (mono-substituted ring C-H), H
NMR (400 MHz, CHCl3-d): δ (ppm): 2.42(s, 3H,=CH3),
3.78(s, 3H, =OCH3), 6.95–6.85(m, 3H, Ar. =CH), 7.21(d, 1H,
Ar. =CH, J: 7.6 Hz), 7.30 (t, Ar. =CH, J: 8.0 Hz), 7.40–7.37(m,
2H, Ar. =CH), 7.82(s, 1H, AR. =CH), 8.14–8.04 (dd, 3H, Ar. =
5. 2-(6-Chloro-2-(Thiophen-2-Yl)Quinolin-4-Yl)Aniline
(4e): The crude substance purified by gravity column
chromatography (ethyl acetate/n-hexane 1:2).