A kind of method for synthesizing aromatic amine compound by palladium/imidazole salt catalyzing nitroaromatic hydrocarbon and amine compound
A technology for amine compounds and nitroaromatic hydrocarbons is applied in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds from amines, etc. Low dosage of ligand, good substrate applicability, and simple operation
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Embodiment 1
[0042]
[0043] In a nitrogen atmosphere, add 92 mg of the above nitroaromatics, 96.4 mg of aromatic amines, and 9.2 mg of Pd(acac) to the dry sealed tube 2 , 15.0mg of imidazolium salt L3, 480mg of tripotassium phosphate trihydrate, 3mL of dioxane, and then tighten the screw cap of the sealing tube, and react at 130°C for 24h. After the reaction was completed, it was filtered with diatomaceous earth, concentrated, and passed through a silica gel column to obtain 119 mg of the product with a yield of 93%.
[0044] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:
[0045] 1 H NMR (400MHz, CDCl 3 )δ7.12–7.04(m,4H),6.95–6.86(m,4H),5.36(bs,1H),3.83(s,3H),2.33(s,3H); 13 C NMR (100MHz, CDCl 3 )δ154.8, 142.5, 136.7, 129.9, 129.3, 121.1, 116.6, 114.7, 55.6, 20.6.
Embodiment 2
[0047]
[0048] Add 120 mg of the above nitroaromatics, 96.4 mg of aromatic amines, and 1.4 mg of Pd(OAc) to the dry sealed tube under nitrogen atmosphere 2 , 30.0mg of imidazolium salt L3, 480mg of tripotassium phosphate trihydrate, 3mL of toluene, then tighten the screw cap of the tube, and react at 130°C for 24h. After the reaction was completed, it was filtered with diatomaceous earth, concentrated, and passed through a silica gel column to obtain 125.9 mg of the product with a yield of 80%.
[0049] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:
[0050] 1 H NMR (400MHz, CDCl 3 )δ7.40–7.30(m,4H),7.29–7.20(m,2H),7.17–7.10(m,2H),6.98(d,J=8.2Hz,2H),6.93–6.83(m,3H) ,5.27(bs,1H),2.20(s,3H); 13 C NMR (100MHz, CDCl 3 )δ140.9, 140.5, 139.1, 131.2, 130.9, 129.9, 129.4, 129.0, 128.3, 127.5, 120.5, 119.4, 116.6, 20.8.
Embodiment 3
[0052]
[0053] In a nitrogen atmosphere, add 92 mg of the above nitroaromatics, 96.4 mg of aromatic amines, and 10.6 mg of PdCl to the dry sealed tube 2 , 45.0mg of imidazolium salt L3, 480mg of tripotassium phosphate trihydrate, 3mL of toluene, then tighten the screw cap of the tube, and react at 130°C for 24h. After the reaction was completed, it was filtered with diatomaceous earth, concentrated, and passed through a silica gel column to obtain 38.2 mg of product with a yield of 30%.
[0054] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:
[0055] 1 H NMR (400MHz, CDCl 3 )δ7.15-7.13(m,1H),7.04–6.96(m,4H),6.81–6.69(m,3H),6.01(bs,1H),3.79(s,3H),2.22(s,3H) ; 13 C NMR (100MHz, CDCl 3 )δ148.0, 139.9, 133.7, 131.2, 129.8, 120.9, 119.7, 119.4, 113.9, 110.4, 55.6, 20.8.
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