Synthesis of 2-(hydroxyphenylamino)- and 2-(aminophenylamino)-4- methylquinolines and N,N′-bis(4-methylquinolin-2-yl)benzenediamines

Article abstract of DOI:10.1134/S1070428013040118

2-(Hydroxyphenylamino)- and 2-(aminophenylamino)-4-methylquinolines and N,N′-bis(4-methylquinolin-2-yl)benzenediamines were synthesized by reactions of 2-chloro-4-methylquinolines with o-, m-, and p-aminophenols and o-, m-, and p-phenylenediamines.

Full text of DOI:10.1134/S1070428013040118

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 4, pp. 559–562. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © I.L. Aleksanyan, L.P. Ambartsumyan, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 4, pp. 576–579.
Synthesis of 2-(Hydroxyphenylamino)- and 2-(Aminophenyl-
amino)-4-methylquinolines and N,N′-Bis(4-methylquinolin-
2-yl)benzenediamines
I. L. Aleksanyan and L. P. Ambartsumyan
Yerevan State University, ul. Aleka Manukyana 1, Yerevan, 375025 Armenia
e-mail: ialeksanyan@ysu.am
Received March 3, 2012
Abstract—2-(Hydroxyphenylamino)- and 2-(aminophenylamino)-4-methylquinolines and N,N′-bis(4-methyl-
quinolin-2-yl)benzenediamines were synthesized by reactions of 2-chloro-4-methylquinolines with o-, m-, and
p-aminophenols and o-, m-, and p-phenylenediamines.
DOI: 10.1134/S1070428013040118
We previously studied reactions of 6(8)-substituted
4-chloro-2-methylquinolines with various nucleo-
philes, including aminophenols and phenylenedi-
amines [1]. Quinoline derivatives possess interesting
pharmacological properties and are widely used for the
preparation of antimalarial drugs. Some aminoquino-
lines exhibit antidepressant, antiviral, antifungal, anti-
tumor, and other activities [2]. With a view to extend
the scope of nucleophilic substitution reactions of
chloroquinolines and obtain new 2-aminoquinoline
derivatives, in the present work we examined (by anal-
ogy with 4-chloroquinolines) reactions of 2-chloro-4-
methylquinolines Ia–Ic with o-, m-, and p-amino-
phenols and o-, m-, and p-phenylenediamines.
2-(Hydroxyphenylamino)-4-methylquinolines IIa–
IIi were synthesized in high yield by heating chloro-
quinolines Ia–Ic with aminophenols at a ratio of 1:1 or
1:1.2 in ethanol in the presence of hydrochloric acid
(Scheme 1). The reactions of Ia–Ic with phenylene-
diamines under similar conditions and even at a ratio
of 1:2 produced mixtures of 2-(aminophenylamino)-4-
methylquinolines IIIa–IIIi and N,N′-bis(4-methyl-
quinolin-2-yl)benzene-diamines IVa–IVi at a ratio of
1:1.2 (Scheme 2).
We succeeded in separating N-mono- and N,N′-di-
substituted phenylenediamines III and IV on the basis
of different solubilities of their hydrochlorides. In
strongly acidic medium, N,N′-disubstituted phenylene-
diamines IV separated from the solution as dihydro-
chlorides, whereas monosubstituted derivatives III
were isolated as free bases from the filtrate.
In order to improve the yield of monosubstituted
phenylenediamines III, the reaction of Ia–Ic with
phenylenediamines was carried out at a reactant ratio
of 1:2.4 in ethanol in the presence of concentrated
hydrochloric acid. In this case, 2-(aminophenylamino)-
4-methylquinolines IIIa–IIIi were formed in almost
quantitative yield.
EXPERIMENTAL
1
The H NMR spectra were recorded on a Varian
Mercury-300 spectrometer from solutions in
DMSO-d6. The purity of the isolated compounds was
Scheme 1.
Me
Me
NH2
3
2'
R
HO
R
OH
·HCl
+
N
Cl
N
N
H
Ia–Ic
IIa–IIi
I, R = H (a), 6-Me (b), 8-Me (c); II, R = H, 2′-OH (a), 3′-OH (b), 4′-OH (c); R = 6-Me, 2′-OH (d), 3′-OH (e), 4′-OH (f);
R = 8-Me, 2′-OH (g), 3′-OH (h), 4′-OH (i).
559

ALEKSANYAN, AMBARTSUMYAN
560
Scheme 2.
Me
1:2.4
R
NH2
N
N
H
Me
N
NH2
IIIa–IIIi
R
H2N
+
Me
N
Cl
Me
R
Ia–Ic
1:1 to 1:2
R
N
H
·2HCl
N
N
H
IVa–IVi
I, R = H (a), 6-Me (b), 8-Me (c); III, IV, R = H: 2′-NH2 (a), 3′-NH2 (b), 4′-NH2 (c); R = 6-Me: 2′-NH2 (d), 3′-NH2 (e) 4′-NH2 (f);
R = 8-Me: 2′-NH2 (g), 3′-NH2 (h), 4′-NH2 (i).
checked by TLC on Silufol UV-254 plates; spots were
developed with iodine vapor.
4-(4-Methylquinolin-2-ylamino)phenol hydro-
chloride (IIc). Yield 2.41 g (84%), mp 271–272°C,
Rf 0.53 (ethanol–toluene, 1:10). Found, %: C 67.19;
H 5.11; N 9.91. C16H15ClN2O. Calculated, %: C 67.02;
H 5.24; N 9.77.
2-(4,6-Dimethylquinolin-2-ylamino)phenol
hydrochloride (IId). Yield 2.58 g (86%), mp 227–
228°C (decomp.), Rf 0.67 (ethanol–toluene, 1:3).
Found, %: C 67.68; H 5.50; N 9.54. C17H17ClN2O.
Calculated, %: C 67.89; H 5.66; N 9.32.
(4-Methylquinolin-2-ylamino)phenol hydro-
chlorides IIa–IIi (general procedure). A mixture of
0.01 mol of 2-chloro-4-methylquinoline Ia–Ic,
0.011 mol of o- or m-aminophenol or p-aminophenol
hydrochloride, and 1 ml of concentrated hydrochloric
acid in 50 ml of ethanol was heated for 8–10 h on
a water bath. The solvent was distilled off, the residue
was treated with water, the mixture was filtered,
the filtrate was made alkaline and filtered, the filtrate
was acidified to pH 2–3, and the precipitate was
filtered off.
3-(4,6-Dimethylquinolin-2-ylamino)phenol
hydrochloride (IIe). Yield 2.67 g (89%), mp 297–
1
298°C, Rf 0.62 (ethanol–toluene, 1:3). H NMR spec-
4
trum, δ, ppm: 2.53 s (3H, CH3), 2.68 d (3H, CH3, J =
2-(4-Methylquinolin-2-ylamino)phenol hydro-
3
4
1.0 Hz), 6.76 d.d (1H, Harom, J = 8.1, J = 2.0 Hz),
chloride (IIa). Yield 2.32 g (81%), mp 114–115°C,
3
4
1
6.81 d.d (1H, Harom, J = 7.5, J = 1.8 Hz), 6.86 t (1H,
Rf 0.66 (ethanol–toluene, 1:15). H NMR spectrum, δ,
Harom, 3J = 8.1 Hz), 7.23 s (1H, 3-H), 7.25 t (1H, Harom
,
4
ppm: 2.69 d (3H, CH3, J = 1.0 Hz), 6.90 t.d (1H,
3J = 8.0 Hz), 7.59 d.d (1Harom, J = 8.6, J = 1.6 Hz),
3
4
3
4
Harom, J = 7.6, J = 1.4 Hz), 6.96 br.s (1H, 3-H),
3
3
4
7.73 br.s (1H, Harom), 7.78 d.d (1H, Harom, J = 8.6,
7.11 d.d (1H, Harom, J = 8.1, J = 1.3 Hz), 7.21 d.d.d
4J = 1.6 Hz), 9.64 br.s (1H, NH), 11.28 br.s (1H, OH),
14.52 br.s (1H, HCl). Found, %: C 68.02; H 5.44;
N 9.48. C17H17ClN2O. Calculated, %: C 67.89; H 5.66;
N 9.32.
3
4
(1H, Harom, J = 8.1, 7.4, J = 1.6 Hz), 7.29 d.d (1H,
Harom, 3J = 7.8, 4J = 1.6 Hz), 7.49 d.d.d (1H, Harom, 3J =
4
3
8.1, 7.2, J = 1.2 Hz), 7.75 d.d.d (1H, Harom, J = 8.4,
4
3
4
7.2, J = 1.2 Hz), 7.90 d.d (1H, Harom, J = 8.4, J =
3
4
1.0 Hz), 7.95 d.d (1H, Harom, J = 8.1, J = 1.1 Hz),
10.13 br.s (1H, NH), 10.80 br.s (1H, OH), 14.54 br.s
(1H, HCl). Found, %: C 67.21; H 5.12; N 9.68.
C16H15ClN2O. Calculated, %: C 67.02; H 5.24; N 9.77.
4-(4,6-Dimethylquinolin-2-ylamino)phenol
hydrochloride (IIf). Yield 2.46 g (82%), mp 327–
328°C, Rf 0.57 (ethanol–toluene, 1:3). Found, %:
C 67.95; H 5.79; N 9.22. C17H17ClN2O. Calculated, %:
C 67.89; H 5.66; N 9.32.
3-(4-Methylquinolin-2-ylamino)phenol hydro-
chloride (IIb). Yield 2.49 g (87%), mp 207–208°C,
Rf 0.62 (ethanol–toluene, 1:10). Found, %: C 66.89;
H 5.10; N 9.86. C16H15ClN2O. Calculated, %: C 67.02;
H 5.24; N 9.77.
2-(4,8-Dimethylquinolin-2-ylamino)phenol
hydrochloride (IIg). Yield 2.76 g (92%), mp 252–
1
253°C, Rf 0.66 (ethanol–toluene, 1:4). H NMR spec-
4
trum, δ, ppm: 2.61 d (3H, CH3, J = 0.9 Hz), 2.85 s
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 4 2013

SYNTHESIS OF 2-(HYDROXYPHENYLAMINO)-...
561
3
4
(3H, CH3), 6.64 t.d (1H, 4′-H, J = 7.5, J = 1.6 Hz),
N-(4-Methylquinolin-2-yl)benzene-1,3-diamine
(IIIb). Yield 0.79 g (32%) (a), 2.42 g (97%) (b);
mp 147–148°C, Rf 0.55 (ethanol–toluene, 1:3). Found,
%: C 77.25; H 5.96; N 16.96. C16H15N3. Calculated, %:
C 77.11; H 6.02; N 16.87.
N-(4-Methylquinolin-2-yl)benzene-1,4-diamine
(IIIc). Yield 0.85 g (34%) (a), 2.39 g (93%) (b);
mp 167–168°C, Rf 0.53 (ethanol–toluene, 1:3). Found,
%: C 77.25; H 5.96; N 16.96. C16H15N3. Calculated, %:
C 77.11; H 6.02; N 16.87.
3
4
6.73 d.d (1H, 2′-H, J = 7.9, J = 1.6 Hz), 6.78 s (1H,
3
3-H), 6.85 t (1H, 3′-H, J = 7.5 Hz), 7.12 t (1H, Harom
,
3J = 7.5 Hz), 7.33 d (1H, Harom, J = 6.7 Hz), 7.57 d
(1H, Harom, 3J = 8.4 Hz), 7.66 br.s (1H, 6′-H), 8.86 br.s
(1H, NH), 10.28 br.s (1H, OH), 13.42 br.s (1H, HCl).
Found, %: C 67.75; H 5.38; N 9.19. C17H17ClN2O.
Calculated, %: C 67.89; H 5.66; N 9.32.
3
3-(4,8-Dimethylquinolin-2-ylamino)phenol
hydrochloride (IIh). Yield 2.73 g (91%), mp 279°C,
Rf 0.65 (ethanol–toluene, 1:4). Found, %: C 68.05;
H 5.41; N 9.46. C17H17ClN2O. Calculated, %: C 67.89;
H 5.66; N 9.32.
4-(4,8-Dimethylquinolin-2-ylamino)phenol
hydrochloride (IIi). Yield 2.82 g (94%), mp 311–
312°C, Rf 0.58 (ethanol–toluene, 1:4). Found, %:
C 67.66; H 5.51; N 9.02. C17H17ClN2O. Calculated, %:
C 67.89; H 5.66; N 9.32.
N-(4-Methylquinolin-2-yl)benzenediamines IIIa–
IIIi and N,N′-bis(4-methylquinolin-2-yl)benzenedi-
amines dihydrochlorides IVa–IVi (general proce-
dures). a. A mixture of 0.01 mol of compound Ia–Ic,
1.30 g (0.012 mol) of o-, m-, or p-phenylenediamine,
and 1 ml of concentrated hydrochloric acid in 50 ml of
ethanol was heated for 6–7 h on a water bath. The
solvent was distilled off, the residue was treated with
water, the mixture was filtered, the filtrate was acidi-
fied to pH 2–3, and the precipitate of dihydrochloride
IVa–IVi was filtered off. The filtrate was made alka-
line, and the precipitate of compound IIIa–IIIi was
filtered off and dried.
b. A mixture of 0.01 mol of quinoline Ia–Ic, 2.59 g
(0.024 mol) of o-, m-, or p-phenylenediamine, and
1 ml of concentrated hydrochloric acid in 50 ml of
ethanol was heated for 6–7 h on a water bath. The
solvent was distilled off, the residue was treated with
water, the mixture was filtered, the filtrate was made
alkaline, and the precipitate of compound IIIa–IIIi
was filtered off.
N-(4,6-Dimethylquinolin-2-yl)benzene-1,2-di-
amine (IIId). Yield 0.66 g (25%) (a), 2.40 g (91%)
(b); mp 131–132°C, Rf 0.50 (ethanol–toluene, 1:4).
1H NMR spectrum, δ, ppm: 2.49 s (3H, CH3), 2.58 d
4
(3H, CH3, J = 1.0 Hz), 4.83 br.s (2H, NH2), 6.78 d.d
3
4
(1H, Harom, J = 8.1, J = 2.0 Hz), 6.84 d.d (1H, Harom
,
3J = 7.5, 4J = 1.8 Hz), 6.88 t (1H, Harom, 3J = 8.1 Hz),
7.24 s (1H, 3-H), 7.31 t (1H, Harom, J = 8.0 Hz),
7.53 d.d (1H, Harom, J = 8.6, J = 1.6 Hz), 7.68 br.s
(1H, Harom), 7.74 d.d (1H, Harom, 3J = 8.6 Hz), 9.75 br.s
(1H, NH). Found, %: C 77.68; H 6.61; N 15.79.
C17H17N3. Calculated, %: C 77.57; H 6.46; N 15.97.
3
3
4
N-(4,6-Dimethylquinolin-2-yl)benzene-1,3-di-
amine (IIIe). Yield 1.21 g (46%) (a), 2.24 g (85%) (b);
mp 121–122°C, Rf 0.52 (ethanol–toluene, 1:3).
1H NMR spectrum, δ, ppm: 2.52 s (3H, CH3), 2.63 d
4
(3H, CH3, J = 1.0 Hz), 4.76 br.s (2H, NH2), 6.82 d.d
3
4
(1H, Harom, J = 8.1, J = 2.0 Hz), 6.84 d.d (1H, Harom
,
3J = 7.5, J = 1.8 Hz), 6.91 t (1H, Harom, J = 8.1 Hz),
7.24 s (1H, 3-H), 7.31 t (1H, Harom, J = 8.0 Hz),
7.53 d.d (1H, Harom, J = 8.6, J = 1.6 Hz), 7.68 br.s
(1H, Harom), 7.74 d.d (1H, Harom, 3J = 8.6 Hz), 9.75 br.s
(1H, NH). Found, %: C 77.25; H 6.58; N 16.15.
C17H17N3. Calculated, %: C 77.57; H 6.46; N 15.97.
4
3
3
3
4
N-(4,6-Dimethylquinolin-2-yl)benzene-1,4-di-
amine (IIIf). Yield 0.75 g (28%) (a), 2.24 g (85%) (b);
mp 111–112°C, Rf 0.53 (ethanol–toluene, 1:2). Found,
%: C 77.31; H 6.62; N 15.82. C17H17N3. Calculated, %:
C 77.57; H 6.46; N 15.97.
N-(4-Methylquinolin-2-yl)benzene-1,2-diamine
(IIIa). Yield 0.75 g (30%) (a), 2.39 g (93%) (b);
mp 131–132°C, Rf 0.62 (ethanol–toluene, 1:5). 1H NMR
spectrum, δ, ppm: 2.57 s (3H, CH3), 4.80 br.s (2H,
NH2), 6.60 m (1H, Harom), 6.76 m (1H, Harom), 6.77 s
(1H, 3-H), 6.89 m (1H, Harom), 7.18 s (1H, Har3om),
N-(4,8-Dimethylquinolin-2-yl)benzene-1,2-di-
amine (IIIg). Yield 0.79 g (30%) (a), 2.59 g (98%)
(b); mp 188–189°C, Rf 0.60 (ethanol–toluene, 1:4).
4
1H NMR spectrum, δ, ppm: 2.57 d (3H, CH3, J =
0.9 Hz), 2.90 s (3H, CH3), 4.79 br.s (2H, NH2), 6.61 t.d
3
4
3
(1H, 4′-H, J = 7.5, J = 1.6 Hz), 6.76 d.d (1H, 5′-H,
7.39 d (1H, Harom, J = 7.8 Hz), 7.44 t (1H, Harom, J =
3J = 7.9, J = 1.6 Hz), 6.80 s (1H, 3-H), 6.86 t (1H,
3′-H, J = 7.5 Hz), 7.08 t (1H, Harom, J = 7.5 Hz),
7.33 d (1H, Harom, 3J = 6.7 Hz), 7.55 d (1H, Harom, 3J =
8.4 Hz), 7.64 br.s (1H, 6′-H), 8.03 br.s (1H, NH).
4
3
7.6 Hz), 7.55 m (1H, Harom), 7.73 d (1H, Harom, J =
3
3
8.1 Hz), 8.11 br.s (1H, NH). Found, %: C 76.98;
H 6.23; N 16.73. C16H15N3. Calculated, %: C 77.11;
H 6.02; N 16.87.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 4 2013

ALEKSANYAN, AMBARTSUMYAN
562
Found, %: C 77.74; H 6.23; N 16.23. C17H17N3. Cal-
culated, %: C 77.57; H 6.46; N 15.97.
N-(4,8-Dimethylquinolin-2-yl)benzene-1,3-di-
amine (IIIh). Yield 0.66 g (25%) (a), 2.56 g (97%)
(b); mp 177–178°C, Rf 0.59 (ethanol–toluene, 1:4).
Found, %: C 77.25; H 6.19; N 16.19. C17H17N3. Cal-
culated, %: C 77.57; H 6.46; N 15.97.
N-(4,8-Dimethylquinolin-2-yl)benzene-1,4-di-
amine (IIIi). Yield 0.99 g (38%) (a), 2.46 g (93%) (b);
mp 189–190°C, Rf 0.62 (ethanol–toluene, 1:3). Found,
%: C 77.72; H 6.68; N 15.73. C17H17N3. Calculated, %:
C 77.57; H 6.46; N 15.97.
N,N′-Bis(4,6-dimethylquinolin-2-yl)benzene-1,3-
diamine dihydrochloride (IVe). Yield 1.62 g (33%),
mp 262–263°C, Rf 0.60 (ethanol–toluene, 1:3).
1H NMR spectrum, δ, ppm: 2.68 s (6H, CH3), 2.95 s
3
(6H, CH3), 7.05 s (2H, 3-H), 7.16 t (1H 5′-H, J =
3
4
8.2 Hz), 7.52 t.d (2H, Harom, J = 7.7, J = 1.1 Hz),
3
4
7.61 d.d (2H, Harom, J = 8.1, J = 2.0 Hz), 7.69 d.d
3
4
(2H, Harom, J = 8.1, J = 1.1 Hz), 7.73 d (2H, 4′-H,
3
4
6′-H, J = 8.1 Hz), 8.51 t (1H, 2′-H, J = 2.0 Hz),
9.11 br.s (2H, NH), 12.76 br.s (2H, HCl). Found, %:
C 68.27; H 5.21; N 11.54. C28H26N4·2HCl. Calculated,
%: C 68.43; H 5.30; N 11.41.
N,N′-Bis(4,6-dimethylquinolin-2-yl)benzene-1,4-
diamine dihydrochloride (IVf). Yield 1.67 g (34%),
mp 325–326°C, Rf 0.62 (ethanol–toluene, 1:2.5).
Found, %: C 68.27; H 5.21; N 11.54. C28H26N4·2HCl.
Calculated, %: C 68.43; H 5.30; N 11.41.
N,N′-Bis(4,8-dimethylquinolin-2-yl)benzene-1,2-
diamine dihydrochloride (IVg). Yield 2.11 g (43%),
mp 295–296°C, Rf 0.65 (ethanol–toluene, 1:4). Found,
%: C 68.31; H 5.17; N 11.52. C28H26N4·2HCl. Calcu-
lated, %: C 68.43; H 5.30; N 11.41.
N,N′-Bis(4,8-dimethylquinolin-2-yl)benzene-1,3-
diamine dihydrochloride (IVh). Yield 1.96 g (40%),
mp 299–300°C, Rf 0.60 (ethanol–toluene, 1:3). Found,
%: C 68.54; H 5.23; N 11.49. C28H26N4·2HCl. Calcu-
lated, %: C 68.43; H 5.30; N 11.41.
N,N′-Bis(4-methylquinolin-2-yl)benzene-1,2-di-
amine dihydrochloride (IVa). Yield 1.76 g (38%),
mp 282–283°C, Rf 0.57 (ethanol–toluene, 1:5).
1H NMR spectrum, δ, ppm: 2.68 s (6H, CH3), 7.36 s
(2H, 3-H), 7.43 m (2H, Harom), 7.54–7.67 m (6H,
3
4
H
arom), 7.87 d.d (2H, Harom, J = 8.2, J = 1.1 Hz),
8.20 m (2H, Harom), 11.70 br.s (2H, NH), 14.70 br.s
(2H, HCl). Found, %: C 67.15; H 4.86; N 11.95.
C26H22N4 ·2HCl. Calculated, %: C 67.39; H 4.75;
N 12.09.
N,N′-Bis(4-methylquinolin-2-yl)benzene-1,3-di-
amine dihydrochloride (IVb). Yield 1.94 g (42%),
mp 211–212°C, Rf 0.67 (ethanol–toluene, 1:4).
1H NMR spectrum, δ, ppm: 2.62 s (6H, CH3), 6.98 s
3
(2H, 3-H), 7.19 t (1H, 5′-H, J = 8.2 Hz), 7.22 m (2H,
3
4
N,N′-Bis(4,8-dimethylquinolin-2-yl)benzene-1,4-
diamine dihydrochloride (IVi). Yield 1.57 g (32%),
mp 363–364°C, Rf 0.61 (ethanol–toluene, 1:4).
1H NMR spectrum, δ, ppm: 2.58 s (6H, CH3), 2.69 s
(6H, CH3), 7.05 s (2H, 3-H), 7.38 t (2H, Harom),
Harom), 7.48 t.d (2H, Harom, J = 7.7, J = 1.1 Hz),
3
4
7.58 d.d (2H, Harom, J = 8.1, J = 2.0 Hz), 7.74 d.d
(2H, Harom, J = 8.1, J = 1.1 Hz), 7.76 d (2H, 4′-H,
6′-H, J = 8.1 Hz), 8.46 t (1H, 2′-H, J = 2.0 Hz),
8.99 br.s (2H, NH), 12.56 br.s (2H, HCl). Found, %:
C 67.22; H 5.08; N 12.16. C26H22N4·2HCl. Calculated,
%: C 67.39; H 4.75; N 12.09.
3
4
3
4
3
7.81 br.s (4H, C6H4), 7.92 d (2H, Harom, J = 8.0 Hz),
3
8.04 d (2H, Harom, J = 8.0 Hz), 9.23 br.s (2H, NH),
12.68 br.s (2H, HCl). Found, %: C 68.32; H 5.41;
N 11.51. C28H26N4·2HCl. Calculated, %: C 68.43;
H 5.30; N 11.41.
N,N′-Bis(4-methylquinolin-2-yl)benzene-1,4-di-
amine dihydrochloride (IVc). Yield 1.90 g (41%),
mp 253–254°C, Rf 0.67 (ethanol–toluene, 1:4).
1H NMR spectrum, δ, ppm: 2.65 s (6H, CH3), 7.10 s
(2H, 3-H), 7.43 m (2H, Harom), 7.70 m (2H, Harom),
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7.97 d (2H, Harom, J = 8.0 Hz), 8.99 br.s (2H, NH),
12.56 br.s (2H, HCl). Found, %: C 67.19; H 4.92;
N 11.98. C26H22N4·2HCl. Calculated, %: C 67.39;
H 4.75; N 12.09.
N,N′-Bis(4,6-dimethylquinolin-2-yl)benzene-1,2-
diamine dihydrochloride (IVd). Yield 2.41 g (49%),
mp 309–310°C, Rf 0.55 (ethanol–toluene, 1:6). Found,
%: C 68.56; H 5.19; N 11.34. C28H26N4·2HCl. Calcu-
lated, %: C 68.43; H 5.30; N 11.41.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 4 2013