MOKHOV et al.
644
Hydrazones 5а‒5d. A solution of m mol of
NMR spectrum, δ, ppm: 1.1 s (6H, 2CH3), 1.70‒1.99
m (15H, Ad), 7.9 s (1Н, Ph), 8.1 s (1Н, Ph), 8.8 s (1Н,
Ph), 8.4 s (1H, CH=N), 11.3 s (1H, NH). Mass spec-
trum, m/z (Irel, %): 386 (2.3) [M]+, 135 (100) [Ad]+, 41
(9.4) [С3Н5]+. Found, %: С 62.22; Н 6.86; N 14.57.
C20H26N4O4. Calculated, %: С 62.16; Н 6.78; N 14.50.
М 386.2.
aldehyde in 5 mL of ethanol was added to a stirred
mixture of n mol of dinitrophenylhydrazine 4, 10 mL
of H2SO4, 15 mL of H2O, and 30 mL of ethanol. The
reaction mixture was held for 15 min at 25°С, and the
crystals that formed were filtered off and recrystallized
from isopropanol.
1-[2-(Adamantan-1-yl)propylidene]-2-(2,4-di-
nitrophenyl)hydrazine (5a) was prepared from 2.4 g
(0.012 mol) of dinitrophenylhydrazine 4 and 0.01 mol
of aldehyde 3a. Yield 3.4 g (0.009 mol, 84%), yellow
FUNDING
The work was funded by the Ministry for Education
and Science of the Russian Federation in the
framework of the basic part of the State order for
2017–2019 (project no. 4.7491.2017/BCh) using the
equipment purchased under the Program for Strategic
Development of the Volga State Technical University
for 2012–2016.
1
crystals, mp 80‒81°С. Н NMR spectrum, δ, ppm:
0.95‒0.97 m (3H, CH3), 1.68‒2.0 m (15H, 1-Ad), 2.0‒
2.1 m (1Н, СН), 7.92 s (1Н, Ph), 8.2 s (1Н, Ph), 8.85 s
(1Н, Ph), 8.59 s (1H, CH=N), 11.35 s (1H, NH). Mass
spectrum, m/z (Irel, %): 372 (1) [M]+, 135 (14) [Ad]+,
41 (100) [С3Н5]+. Found, %: С 61.34; Н 6.56; N 15.12.
C19H24N4O4. Calculated, %: С 61.28; Н 6.50; N 15.04.
М 372.2.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
REFERENCES
1-[2-(Adamantan-1-yl)pentylidene]-2-(2,4-di-
nitrophenyl)hydrazine (5b) was prepared similarly
from 2.2 g (0.011 mol) of hydrazine 4 and 2 g (0.009 mol)
of aldehyde 3b. Yield 3.5 g (0.0084 mol, 93%); yellow
1
crystals, mp 178‒180°С (i-PrOH). Н NMR spectrum,
1. Butov, G.M. and Mokhov, V.M., Russ. J. Org.
Chem., 2018, vol. 54, p. 1760. doi 10.1134/
S1070428018120035
δ, ppm: 0.91‒0.94 m (3H, CH3), 1.45‒1.49 m (4Н,
2СН2), 1.59‒1.97 m (15H, Ad), 1.98‒2.0 m (1Н, СН),
7.9 s (1Н, Ph), 8.25 s (1Н, Ph), 9.0 s (1Н, Ph), 7.94 s
(1H, CH=N), 11.12 s (1H, NH). Mass spectrum, m/z
(Irel, %): 400 (2.2) [M]+, 135 (22) [Ad]+, 41 (100)
2. Stepanov, F.N. and Dovgan’, N.L., Zh. Org. Khim.,
1968, vol. 4, p. 277.
3. Polis, Ya.Yu., Raugel’, B.P., and Liepin’sh, E.E., USSR
Inventor’s Certificate no. 1793313, 1977; Byull.
Izobret., 1977, no. 5.
+
[С3Н5]+, 233 (11) [M ‒ C6H3(NO2)2 ]. Found, %: С
63.01; Н 7.12; N 13.80. C21H28N4O4. Calculated, %: С
62.98; Н 7.05; N 13.99. М 400.2.
4. Voloboev, S.N., Butenko, L.N., and Novakov, I.A.,
Russ. J. Gen. Chem., 2001, vol. 71, p. 1121. doi
10.1023/A:1013178326353
1-[2-(Adamantan-1-yl)hexylidene]-2-(2,4-di-
nitrophenyl)hydrazine (5с) was prepared similarly
from 2 g (0.01 mol) of hydrazine 4 and 2 g (0.0085 mol)
of aldehyde 3с. Yield 3.6 g (0.0083 mol, 98%); yellow
5. Bott, K., Angew. Chem., 1968, vol. 80, p. 970. doi
10.1002/ange.19680802211
1
6. Kell, D.R. and McQuill, F.J., J. Chem. Soc., D: Chem.
Commun., 1970, p. 599. doi 10.1039/C29700000599
crystals, mp 167‒168°С (i-PrOH). Н NMR spectrum,
δ, ppm: 0.85‒0.9 m (3H, CH3), 1.39‒1.42 (6Н, 3СН2),
1.55‒1.95 m (15H, Ad), 1.97‒1.99 m (1Н, СН), 7.60 s
(1H, CH=N), 7.80 s (1Н, Ph), 8.24 s (1Н, Ph), 9.0 s
(1Н, Ph), 11.0 s (1H, NH). Mass spectrum, m/z (Irel,
%): 414 (8) [M]+, 135 (100) [Ad]+, 41 (18) [С3Н5]+.
Found, %: С 63.82; Н 7.34; N 13.66. C22H30N4O4.
Calculated, %: С 63.75; Н 7.30; N 13.52. М 414.2.
7. Buckle, M.J.C., Fleming, I., Gil, S., and Pang, K.L.Ch.,
Org. Biomol. Chem., 2004, vol. 2, p. 749. doi 10.1039/
B313446F
8. No, B.I., Butov, G.M., Mokhov, V.M., and Parshin, G.Yu.,
Russ. J. Org. Chem., 2002, vol. 38, 295. doi 10.1023/
А:1015598607917
9. No, B.I., Butov, G.M., Mokhov, V.M., and Parshin, G.Yu.,
Russ. J. Org. Chem., 2002, vol. 38, p. 1377. doi
10.1023/A:1021680519152
1-[2-(Adamantan-1-yl)-2-methylpropylidene]-2-
(2,4-dinitrophenyl)hydrazine (5d) was prepared simi-
larly from 2.3 g (0.011 mol) of hydrazine 4 and 2 g
(0.01 mol) of aldehyde 3d. Yield 3.8 g (0.0094 mol,
10. Mokhov, V.M., Butov, G.M., and Saad, K.R., Russ.
J. Org. Chem., 2014, vol. 50, p. 1276. doi 10.1134/
S1070428014090073
1
96%); yellow crystals, mp 250‒251°С (i-PrOH). Н
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 5 2019