A kind of C5 selective halogenation method of amide quinoline derivative
A technology of amide quinoline and amide quinoline, which is applied in the direction of organic chemistry, can solve problems such as unsuitable amide compounds, and achieve the effects of protecting the health of environmental operators, ensuring the health of operators, and promoting development
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[0022] The invention provides a method for preparing a C5 selective halide of amide quinoline derivatives, comprising the following steps: taking N-(8-quinolyl) amide and sodium halide as reaction substrates, and the molar ratio range of the two 1:1~1:1.2; by adding 100~200 mol% of potassium persulfate, iodobenzene diacetate or manganese acetate trihydrate (Ⅲ) as an oxidant, in acetonitrile, toluene or 1,4-dioxane In the solvent of one of the reactions, react at a temperature of 70°C to 100°C for 12h to 24h; the chemical reaction formula is as follows:
[0023]
[0024] The R 1 phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 4-biphenyl One of base, 2-naphthyl, ethyl, cyclohexyl, benzyl, and 1-furyl; X is one of chlorine, bromine, and iodine; Y can be an N atom or a C atom;
[0025] Wherein the quinoline group in the N-(8-quinolyl) amide in the substrate can also be replaced by naphthalene or phenyl,
[0026...
specific Embodiment 1
[0027] Specific embodiment one: with 49.6 milligrams (0.2mmol) N -(8-quinolyl)benzamide, 12.8 mg (0.22 mmol) of sodium chloride, and 81.1 mg (0.3 mmol) of potassium persulfate were added to 2 mL of acetonitrile solvent. Reacted at 70°C for 24 hours, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove the solvent. The residue was subjected to silica gel column chromatography, rinsed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 20:1, and The effluent was collected in the actual gradient, detected by TLC, and the effluent containing the product was combined, the solvent was distilled off by a rotary evaporator, and 30 mg of a white solid was obtained by vacuum drying. 8-benzamido-5-chloroquinoline, yield 53%. 1 H NMR (500 MHz, CDCl 3 ) δ 10.67 (s, 1H), 8.89-8.87 (m, 2H), 8.58 (d, J =8.5 Hz, 1H), 8.07 (d, J = 8.0 Hz, 2H), 7.65 (d, J = 8.5 Hz, 1H), 7.61-7.54(m, 4H). 13 C NMR (125 MHz, CDCl 3 ) δ 165.5...
specific Embodiment 2
[0028] Specific embodiment two: with 52.5 milligrams (0.2mmol) N -(8-quinolyl)p-toluamide, 12.8 mg (0.22 mmol) of sodium chloride, and 81.1 mg (0.3 mmol) of potassium persulfate were added to 2 mL of acetonitrile solvent. Reacted at 70°C for 24 hours, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove the solvent. The residue was subjected to silica gel column chromatography, rinsed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 20:1, and The effluent was collected in actual gradient, detected by TLC, the effluent containing the product was combined, the solvent was distilled off by a rotary evaporator, and 29.7 mg of a white solid was obtained by vacuum drying. 8-(4-methylbenzamido)-5-chloroquinoline, yield 50%. 1 H NMR (500 MHz, CDCl 3 ) δ 10.61 (s, 1H), 8.86-8.84 (m, 2H), 8.54 (d, J = 8.5 Hz, 1H), 7.95 (d, J = 7.5 Hz, 2H), 7.61 (d, J = 7.5 Hz ,1H), 7.55 (dd, J = 8.5, 4.0 Hz, 1H), 7.33 (d, J = 7...
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