* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With hydrogenchloride; phosphoric acid In water at 80℃; for 4 h;
5.0 g of 4-amino-3-nitrophenol (compound a, 32 mmol), 40 mL of concentrated hydrochloric acid and 15 g of concentrated phosphoric acid were added to a reaction vessel and heated to 80 ° C., 6.5 mL (97 mmol) of acrolein was slowly added added. After reacting for 4 hours, the reaction solution was allowed to cool to room temperature, distilled water was added, and the mixture was filtered through Celite (Celite Corporation). The filtrate was neutralized with aqueous ammonia to give a red precipitate. The precipitate was collected by filtration and dried under vacuum to give a red solid (yield: 3.0 g, yield: 49percent).
Reference：
[1] Chemical Communications, 2015, vol. 51, # 46, p. 9539 - 9542
[2] Patent: JP2015/20986, 2015, A, . Location in patent: Paragraph 0070
[3] Inorganic Chemistry, 2010, vol. 49, # 20, p. 9535 - 9545
(1) diazotization reaction: take 12g3_ amino-4-nitrophenol,Dissolved in 64 g of hydrobromic acid at a concentration of 40 wtpercentLiquid, cooled to 0-10 ° C.36 g of a 20percent by weight aqueous solution of sodium nitrite was added dropwise at this temperature. Thermal insulation reaction 1h.The resulting yellow liquid was an aqueous solution of 3-nitrophenol-4-diazonium salt, which was used directly in the next reaction.(2) Bromination reaction:Take 1.2g cuprous bromide, dissolved in 27g concentration of 40wtpercent hydrobromic acid solution.After the temperature was raised to 40-45 ° C, the reaction solution obtained in step (1) was added dropwise. After the addition was completed, the reaction 1h Thermal insulation. Cool to 20-25 ° C, precipitated solid. The product is filtered off and the solid washed with a little water and dried.13.1 g of 3-nitro-4-bromophenol were obtained.Content of 95percent.
In DMF (N,N-dimethyl-formamide); at 150℃; for 0.166667h;Microwave;
Step 2.Synthesis of 2-nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine A solution of 4-amino-3-nitro-phenol (1 eq) and <strong>[483324-01-2]2-chloro-4-(3-pyridyl)pyrimidine</strong> (1 eq) in N,N-dimethylformamide was microwaved at 150 C. for 10 mins.The reaction mixture was partitioned between ethyl acetate and water.The organic layer was concentrated and purified on silica gel to yield 2-nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine. MS: MH+=309.
(0.11 mole) of <strong>[3386-35-4]n-octyl tosylate</strong>, 15.4 g (0.1 mole) of 4-hydroxy-2-nitroaniline and 16.6 g (0.12 mole) of potassium carbonate were dissolved in 200 ml of acetonitrileThe reaction was refluxed until the 4-hydroxy-2-nitroaniline disappeared.The reaction was terminated by TLC (Thin layer Chromatography). After cooling to room temperature, acetonitrile was removed under reduced pressure, and 300 g of water was added to the residue. The resultant solid was filteredThe filtered solid was washed with 300 g of water and vacuum dried to obtain 26.1 g of the desired compound (yield: 98%, purity: 99.2%).
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