Asian Journal of Chemistry; Vol. 32, No. 1 (2020), 195-198
A
SIAN
J
OURNAL OF HEMISTRY
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Synthesis, Characterization and Crystal Structure of 2-Pyridinecarboxamide
1
2,*
KAI-JIN SUN and ZHAO-SHENG CAI
1Jiuzhou Pharmaceutical College, Yancheng Vocational Institute of Industry Technology, Yancheng 224005, Jiangsu Province, P.R. China
2School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051, Jiangsu Province, P.R. China
*Corresponding author: Fax: +86 515 88583907; E-mail: jsyc_czs@163.com; hgxskj@126.com
Received: 13 August 2019;
Accepted: 4 October 2019;
Published online: 18 November 2019;
AJC-19697
2-Pyridinecarboxamide was synthesized from 2-picoline through two-steps reaction. Initially, 2-picoline was converted into 2-cyanopyridine
by ammoxidation in a stainless-steel fixed-bed reactor at 370 ºC withV2O5 loaded on TiO2 as catalyst. The 2-cyanopyridine was transformed
into 2-pyridinecarboxamide through oxidation hydrolysis in basic solution using MnO2 as oxidant at 70 ºC. The final product was
characterized by FT-IR, NMR and UV-visible analysis, and 2-pyridinecarboxamide in the final product was determined using HPLC. The
crystal structure of 2-pyridinecarboxamide was investigated using X-ray diffraction and SHELX 2018/3 (sh) software and the result
indicated that 2-pyridinecarboxamide crystallized in the monoclinic system, space group P21/n with a = 5.207(2), b = 7.097(3), c =
16.243(6) Å, V = 595.7 (4) Å3; Z = 4.
Keywords: 2-Picoline, 2-Pyridinecarboxamide, Crystal structure.
All chemicals were of reagent grade and used without further
purification as received.
INTRODUCTION
The importance of pyridinecarboxamide as pharmaceu-
tical and agricultural intermediates has been well established.
For example, 2-pyridinecarboxamide could be used for synthesis
of antipsychotic drugs [1], glucokinase activators [2] and as
ligand in the formation of La(III) and Ce(III) complexes [3].
3-Pyridinecarboxamide is the key intermediate for preparing
imidazo[4,5-c]pyridinecarboxamide derivatives that could be
utilized as PARP-1 inhibitors [4]. There are several methods
could be utilized for preparing pyridinecarboxamide, such as
aminification reaction of pyridinecarboxylic acid or its deriva-
tives with ammonia [5], controlled hydrolysis of cyanopyridine
[6] and conversion of pyridinecarboxaldehyde with hydroxyl-
amine [7], etc. Herein, we report the synthesis of 2-pyridine-
carboxamide from 2-picoline through two-steps, which includes
ammoxidation and oxidation hydrolysis. The crystal structure
of 2-pyridinecarboxamide also was investigated.
Fourier transform infrared (FT-IR) spectrum was recorded
with KBr pellets on a Nicolet Nexux FT-IR 670 spectrometer,
sixteen scans at a resolution of 4 cm-1 were averaged and refer-
enced against air. 1H NMR spectrum was obtained with Bruker
AV-500 spectrometer at 500.13 MHz and measured in D2O
solution at 30 0.5 ºC and the sample was dissolved in a 5 mm
diameter tube at a concentration of about 20 mg mL-1. UV-
visible spectrum was obtained with TU-1810 ultraviolet-visible
spectrophotometer with scan interval was 400~190 nm and
water as solvent. The contents of final product was determi-
nated by L600 high performance liquid (HPLC) chromato-
graphy and X-ray diffraction was performed on a BrukerAPEXII
CCD diffractometer.
Preparation of catalyst: The catalyst of V2O5 loaded on
TiO2 was prepared according to reported method [8] with some
modification. Briefly, 150 g of TiO2 and 20 g of NH4VO3 were
added to 50 mL deionized water. The mixture was formed into
a cylindrical catalyst of 5~7 mm length and 2~4 mm diameter.
The cylindrical catalyst was dried for 1.0 h at 60 ºC, then calcined
for 2.0 h at 250 ºC and for 5.0 h at 750 ºC in muffle furnace.
The content of V2O5 loading in catalyst was 8.3 mol %.
EXPERIMENTAL
2-Picoline, vanadium pentoxide (V2O5) , titanium dioxide
(TiO2) and manganese dioxide (MnO2) were purchased from
Sinopharm Chemical Reagent Co. Ltd. (Shanghai, P.R. China).
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