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Compound of monoimine pyridine, preparation method and catalyst containing the compound and application

A technology of monoiminopyridine and compound, which is applied in the field of monoiminopyridine compound to achieve the effects of improved yield, high yield and easy operation

Inactive Publication Date: 2005-08-31
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A great deal of work has been devoted to the modification and modification of the imine group on pyridinediimine, while the modification of its precursor has been rarely explored

Method used

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  • Compound of monoimine pyridine, preparation method and catalyst containing the compound and application
  • Compound of monoimine pyridine, preparation method and catalyst containing the compound and application
  • Compound of monoimine pyridine, preparation method and catalyst containing the compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1. Synthesis of monoimine pyridine compound precursor 2-acetyl-6-ethoxypyridine:

[0035] Using 2,6-lutidine as raw material, 2,6-dicarboxylic acid pyridine was prepared by oxidation of potassium permanganate (Singer, A.W.; McElvain, S.M.J.Am.Chem.Soc.1935, 57, 1135. Beilstein Handbook of Organic Chemistry, fifth Supplementary Series, Springer-Verlag, Berlin, 1990, Vol.22, part 4, 128.), and then prepare 2,6-dicarboxypyridine by esterification. The preparation procedure was simplified from the literature method and gave a higher yield (83%) than the literature value (60%) (Barnes, R.A.; Fales, H.M.J. Am. Chem. Soc. 1953, 75, 3830.). Then 2,6-dicarboxypyridine was dissolved in freshly distilled EtOAc, treated with dry sodium alkoxide powder, and then refluxed with excess concentrated hydrochloric acid to finally obtain the product 2-acetyl-6-carboxypyridine .

[0036] Sodium flakes (2.10 g, 91 mmol) were added into 60 mL of absolute ethanol. After the sodium flakes wer...

Embodiment 2

[0044] 1. Synthesis of monoimine pyridine compound 2-carboethoxy-6-{1-[(2,4,6-trimethylphenyl)imine]ethyl}pyridine:

[0045] Add 2-acetyl-6-carboethoxypyridine (0.772g, 4.0mmol) and excess 2,4,6-trimethylaniline (1.08g, 8.0mmol) prepared in Example 1 into a 25mL conical flask middle. The Erlenmeyer flask was put into a microwave oven (Media), and reacted for 20 minutes under high fire (800W) conditions. The obtained crude product was purified by chromatography (silica gel column 60×2.5 cm, eluent: petroleum ether:ethyl acetate=2:1). A light yellow solid was obtained with a yield of 74.1%. mp 75.0-76.0℃. 1 H NMR (400MHz, CDCl 3 ): δ8.56(d, 1H, Py-Hm), 8.19(d, 1H, Py-Hm), 7.94(t, 1H, Py-Hp), 6.90(s, 2H, Ar-Hm), 4.88( m, 2H, CH 2 ), 2.26(d, 3H, N=C(Me)), 2.06(s, 6H, Ar-Me), 1.47(t, 3H, CH 2 (CH 3 )).IR(KBr):ν C＝O 1715cm -1 , ν C＝N 1643cm -1 , ν C-O-C 1137cm -1 .Elemental analysis C 19 h 22 N 2 o 2 Theoretical value: C, 73.52; H, 7.14; N, 9.03. Found value: C, 73...

Embodiment 3

[0051] 1. Synthesis of monoimine pyridine compound 2-carboethoxy-6-{1-[(2,6-diethylphenyl)imine]ethyl}pyridine:

[0052] Add 2-acetyl-6-carboethoxypyridine (0.670 g, 3.5 mmol) and excess 2,6-diethylaniline (1.07 g, 7.2 mmol) prepared in Example 1 into a 25 mL Erlenmeyer flask. The Erlenmeyer flask was put into a microwave oven (Media), and reacted for 35 minutes under high fire (800W) conditions. The obtained crude product was separated by chromatography (silica gel column 30×1.5cm, eluent: n-hexane:dichloromethane=1:2, silica gel column 40×1.5cm, eluent: ether:petroleum ether=2:3), The product was purified to obtain a light yellow solid with a yield of 17.6%. mp84.0-86.0℃. 1 H NMR (400MHz, CDCl 3 ): δ8.48(d, 1H, Py-Hm), 8.11(d, 1H, Py-Hm), 7.87(t, 1H, Py-Hp), 7.30(d, 2H, Ar-Hm), 6.99( t, 1H, Ar-Hp), 4.43 (m, 2H, COOCH 2 ), 2.28(m, 4H, (CH 2 )CH 3 ), 2.20(s, 3H, N=C(Me)), 1.39(t, 3H, COOCH 2 (CH 3 )), 1.05(t, 6H, CH 2 (CH 3 )).IR(KBr):ν C＝O 1742.3cm -1 , ν C＝N 16...

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Abstract

A monoimine pyridine compound is prepared through proportionally mixing 2-acetyl-6-ethoxycarbonyl pyridine with substituted amine, microwave radiation reaction to obtain coarse product, and purifying by chromatography. The catalyst containing said compound and its application are also disclosed.

Description

technical field [0001] The present invention relates to a monoimine pyridine compound, a preparation method thereof, a catalyst containing the compound and its application in ethylene polymerization catalysis. Background technique [0002] In recent years, research on late transition metal complex catalysts for ethylene polymerization and oligomerization has been rapidly developed. 1998 M.Brookhart (B.L.Small, M.Brookhart, A.M.A.Bennett, J.Am.Chem.Soc., 1998, 120, 4049; A.M.A.Bennett, CHEMTECH., 1999, 29, 24; B.L.Small, M.Brookhart, Macromolecules, 1999, 32, 2120.) and V.C.Gibson (G.J.P.Britovsek, V.C.Gibson, B.S.Kimberley, P.J.Maddox, S.J.McTavish, G.A.Solan, A.J.P.White, D.J.Williams, Chem.Commun., 1998, 849; G.J.P.B .Bruce, V.C.Gibson, B.S.Kimberley, P.J.Maddox, S.Mastroianni, S.J.McTavish, C.Redshaw, G.A.Solan, S.Strömberg, A.J.P.White, D.J.Williams, J.Am.Chem.Soc., 1999, 121, 8728.) Research groups almost simultaneously reported Fe(II) and Co(II) complexes of pyridine...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07D213/79C08F4/80C08F10/02
Inventor 苏碧云赵建设
Owner NORTHWEST UNIV
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