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DOI: 10.1039/C6RA15922B
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(0.929 g) [24, 25]. Then, nitric acid 100% (0.315 g, 5 mmol) was
65
70
dropwise added to [PySO3H]Cl (0.993 g, 5 mmol) over a period
of 5 min at room temperature under a continuous flow of nitrogen
to remove the HCl gas that is produced. The resulting mixture
was stirred for 10 min under these conditions to give [Pyridine–
SO3H]NO3 as a viscous yellow red oil in 97% yield.
5
1ꢀsulfopyridinium nitrate. Yellow Red oil; IR (Nujol) cm−1; 1183,
1308, 1543, 3100ꢀ3600; 1H NMR (300 MHz, DMSOꢀd6) δ (ppm)
8.11ꢀ8.14 (t, J = 9 Hz, 2H), 8.64ꢀ8.69 (m,1H), 8.95ꢀ8.97 (d, J = 6
10 Hz, 2H), 11.37 (s, 1H); 13C NMR (75 MHz, DMSOꢀd6) δ (ppm)
127.85, 142.17, 147.23. Anal. Calcd (%) for C5H6N2O6: C, 25.03;
H, 3.36; N, 11.66; S, 13.35. Found: C, 24.22; H, 3.115; N, 11.95 ;
S, 13.51.
75
2.3. General Procedure for the Nitration of Compounds.
15 To a roundꢀbottomed flask (10 mL) was added [Pyridine–
SO3H]NO3 (0.222 g, 1 mmol). The aromatic compound (1 mmol)
was then added, and the mixture was stirred at room temperature.
After the reaction was completed (monitored with TLC),
dichloromethane (5 mL) was added to the reaction mixture, and
20 the mixture was stirred for 2 min and separated. The organic
solvent was evaporated, and the product was easily purified by
short column chromatography. Note: For the nitration of aniline,
after the reaction was completed, the reaction mixture was
basified to pH 8 by the slow addition of 10% NaOH solution. The
25 organic layer was separated, and the aqueous layer was extracted
with dichloromethane. The combined organic solution was
washed with brine, dried over MgSO4, filtered, and concentrated
to give a crude product, which was purified with short column
chromatography.
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30 Notes and references
aDepartment of Chemistry, Sayyed Jamaleddin Asadabadi University,
Asadabad 6541835583, Iran
bFaculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683,
Iran
35 cDepartment of Chemistry and Chemical Biology, Harvard University, 12
Oxford St., Cambridge MA 02138, USA
† Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/b000000x/
40 ‡ Footnotes should appear here. These might include comments relevant
to but not central to the matter under discussion, limited experimental and
spectral data, and crystallographic data.
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