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Stage #1: With hydrogenchloride In water for 12 h; Reflux Stage #2: With sodium hydroxide In water
General procedure: 3-aminocrotononitrile (48, 10 mmol) was added to a suspension of the appropriate arylhydrazine 49a-l (10 mmol) in 12M HCl-H2O (12 mL, 1:3), and the resulting mixture was heated under reflux for 12 hours and then cooled and neutralized with 2.5M sodium hydroxide solution. The suspension was extracted with CH2Cl2 (3x30 mL). The organic phases were washed with brine (20 mL), dried and the solvent evaporated in vacuo. The residue oil was triturated with hexane to obtain a solid which was separated by filtration. Subsequent chromatography was performed where indicated.
60%
Stage #1: With hydrogenchloride In water at 100℃; for 18 h; Stage #2: With sodium hydroxide In water
2.789 g (15.83 mmol) of 2-(trifluoromethyl)-phenylhydrazine was prepared in 15 ml of IN hydrochloric acid and 1.378 g (16.781 mmol) of 3-aminocrotonic nitrile was added. The mixture was stirred for 18 h at 1000C. After cooling, the pH value of the mixture was adjusted with IN sodium hydroxide solution to pH > 12. It was extracted with dichloromethane three times. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in a rotary evaporator at reduced pressure. The product was dried at high vacuum and purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80 -->90:10). We obtained 2.50O g (60percent of theor., purity 91percent according to HPLC) of the target compound.LC-MS (method 10): R, = 1.09 min; MS (EIpos): m/z = 242 [M+H]+.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3429 - 3445
[2] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 136-137
[3] Journal of Combinatorial Chemistry, 2010, vol. 12, # 4, p. 510 - 517
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