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Preparation method of primary amine and secondary amine compound
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A technology of primary amine and titanium trichloride, applied in the field of preparing primary amine and secondary amine, to achieve the effect of wide application scope of substrates, extended application scope and low price
Inactive Publication Date: 2012-12-05
SICHUAN UNIV
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Embodiment 1
[0030] Embodiment 1: the reductive cleavage of phenylhydrazine
[0031]
[0032] Under the protection of nitrogen, phenylhydrazine (10 mmol) was dissolved in 10 mL of THF, then an aqueous solution of titanium trichloride (15%, 40 mL) was added, and stirred under reflux for 4 hours. After the reaction is completed, post-treatment is carried out according to Method 2 to obtain aniline with a yield of 90%.
Embodiment 2
[0033] Example 2: Reductive Cleavage of 6-Bromo-2-Naphthylhydrazine
[0034]
[0035] The experimental operation was similar to that of Example 1, except that 6-bromo-2-naphthylhydrazine was dissolved in a mixed solution of ethanol and DMF for reaction. After the reaction, it was treated according to method 1 to obtain a white solid with a yield of 90%. 6-Bromo-2-naphthylamine: Mp: 127-128°C; 1 HNMR (600MHz, CDCl 3)δ (ppm): 7.83 (d, J=1.2Hz, 1H), 7.56 (d, J=8.4Hz, 1H), 7.46 (d, J=9.0Hz, 1H), 7.41 (dd, J=8.4Hz , 1.8Hz, 1H), 6.97-6.94(m, 2H), 3.89(brs, 2H); 13 C NMR (100MHz, CDCl 3 )δ (ppm): 144.6, 133.4, 129.7, 129.6, 129.0, 128.4, 127.5, 119.1, 115.7, 108.4.
Embodiment 3
[0036] Example 3: Reductive cleavage of N-n-heptyl-N-(2-naphthalene)hydrazine
[0037]
[0038] The experimental operation was similar to that of Example 1, and N-n-heptyl-2-naphthylamine was obtained as a colorless oil with a yield of 81%. 1 H NMR (400MHz, CDCl 3 )δ(ppm): 7.65(d, J=8.0Hz, 1H), 7.60(d, J=8.4Hz, 2H), 7.34(t, J=7.2Hz, 1H), 7.17(t, J=7.2Hz , 1H), 6.85(dd, J=8.4Hz, 2.0Hz, 1H), 6.78(d, J=2.0Hz, 1H), 3.76(brs, 1H), 3.19(t, J=7.2Hz, 2H), 1.69-1.63(m, 2H), 1.48-1.25(m, 8H), 0.90(t, J=6.8Hz, 3H); 13 C NMR (100MHz, CDCl 3 )δ (ppm): 146.4, 135.6, 129.0, 127.9, 127.6, 126.5, 126.1, 122.0, 118.3, 104.3, 44.2, 32.1, 29.7, 29.5, 27.5, 23.0, 14.4.
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Abstract
The invention relates to a method for preparing various primary amines and secondary amines by taking titanium trichloride aqueous solution as reducing agents to reduce substituted hydrazine; the titanium trichloride aqueous solution and the substituted hydrazine are mixed together and heated and refluxed for 0.5-10 hours directly under the protection of nitrogen. The method has the advantages ofcheap and easy-obtained reagents, moderate reaction conditions, wide application range of substrate, simple operation and rapid reaction and the like.
Description
technical field [0001] The invention relates to a new method for preparing primary and secondary amines. The method uses titanium trichloride aqueous solution as a reducing agent to reduce various substituted hydrazine compounds and synthesize corresponding primary and secondary amines. Background technique [0002] Amines are an important class of organic compounds. Many amines are important intermediates and ligands in organic synthesis. At the same time, many amines have good physiological activities and are important drugs. [0003] There are many ways to synthesize amine compounds, each with its own advantages and disadvantages. The preparation of amines by reductive cleavage of hydrazine is one of the effective methods for the synthesis of amine compounds. The most common method for reductive cleavage of hydrazine is catalytic hydrogenolysis, commonly used catalysts are Pd / C, Pd(OH) 2 , PtO 2 , Pt and Raney Ni et al. For example: a bimetallic catalyst composed of ...
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