Process for synthesizing multi-substituent pyridine derivative and dipyridine derivative from nitrile
A synthesis method and derivative technology, applied in silicon organic compounds, organic chemistry, etc., can solve the problems of difficult synthesis of multi-substituted pyridine derivatives, bipyridine derivatives, poor selectivity, low yield, etc., and achieve a scientific and reasonable synthesis method , product is easy, the effect of high yield
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example 1
[0025] One of the I class compounds in the structural formula (R=nPr): 2-phenyl-3,4,5,6-tetra(n-propyl)-pyridine synthesis
[0026] Under the protection of an inert gas (such as high-purity nitrogen), add 1 mmol of 4,7-diiodo-5,6-di(n-propyl )-4,6-quinadiene and 5 mL of anhydrous and oxygen-free treated ether solvent. First, the above ether solution was lowered to a lower temperature (-78°C to -55°C) with a cold bath (such as a dry ice-acetone bath), and then 4 mmol tert-butyllithium (1.6M, n-pentane solution) was added dropwise under magnetic stirring. ). After the reaction was stirred at -78°C to -55°C for 1 hour, 2 mmol of hexamethylphosphoramide and 4 mmol of benzonitrile were added. The cooling bath was removed, and the reaction solution was gradually warmed to room temperature (20°C to 28°C), stirred for 1 hour, and then washed with about 1 mL of saturated NaHCO 3 Aqueous solution quenched the reaction. Extracted three times with petroleum ether (each 10mL). The ext...
example 2
[0028] The second compound of class I in the structural formula (R=nPr, R'=4-methoxyphenyl): 2-(4-methoxyphenyl)-3,4,5,6-tetra(n-propyl) - Synthesis of pyridine.
[0029] The synthetic route is basically the same as above. The starting material diiodide compound in this synthesis is 4,7-diiodo-5,6-di(n-propyl)-4,6-quinadiene, and the starting material nitrile is 4-methoxybenzonitrile. Obtained 0.319 g of pure product (purity>98%, yellow liquid). Isolated yield 80%. The NMR and high-resolution mass spectrometry data of the compound are as follows. 1 H NMR (CDCl 3 , Me 4 Si) δ0.79(t, J=7.2Hz, 3H), 0.98(t, J=7.2Hz, 3H), 1.03-1.13(m, 6H), 1.32-1.44(m, 2H), 1.49-1.62( m, 4H), 1.67-1.80(m, 2H), 2.44-2.54(m, 2H), 2.54-2.68(m, 4H), 2.68-2.79(m, 2H), 3.82(s, 3H), 6.92( d, J=8.4Hz, 2H), 7.32(d, J=8.4Hz, 2H). 13 C NMR (CDCl 3 , Me 4 Si)δ14.42(CH 3 ), 14.59 (CH 3 ), 14.89 (CH 3 ), 15.01 (CH 3 ), 23.63 (CH 2 ), 24.54 (CH 2 ), 24.59 (CH 2 ), 31.00 (CH 2 ), 31.47 (CH 2 ), ...
example 3
[0031] The third compound of class I in the structural formula (R=Et, R'=4-methylphenyl): the synthesis of 2-(4-methylphenyl)-3,4,5,6-tetraethyl-pyridine.
[0032] The synthetic route is basically the same as above. The starting raw material diiodide compound of this synthesis is 3,6-diiodo-4,5-diethyl-3,5-octadiene, and the starting raw material nitrile is 4-methylbenzonitrile. 0.163 g of pure product was obtained (purity>98%, yellow liquid). Isolated yield 58%. The NMR and high-resolution mass spectrometry data of the compound are as follows. 1 H NMR (CDCl 3 , Me 4 Si)δ 1.00(t, J=7.5Hz, 3H), 1.16-1.32(m, 9H). 2.38(s, 3H), 2.58(m, 2H), 2.64-2.77(m, 4H), 2.82(m , 2H), 7.19(d, J=7.8Hz, 2H), 7.29(d, J=7.8Hz, 2H). 13 C NMR (CDCl 3 , Me 4 Si)δ14.64(CH 3 ), 15.35 (CH 3 ), 15.43 (CH 3 ), 15.63 (CH 3 ), 21.25 (CH 3 ), 21.42 (CH 2 ), 21.77 (CH 2 ), 22.03 (CH 2 ), 28.33 (CH 2 ), 128.66(2CH), 128.74(2CH), 132.47(C), 133.17(C), 136.72(C), 139.53(C), 149.21(C), 156.67(C),...
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