* 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.
Reference：
[1] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3047 - 3062
[2] Organic Letters, 2003, vol. 5, # 14, p. 2413 - 2415
[3] Tetrahedron Letters, 2001, vol. 42, # 23, p. 3917 - 3919
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Reference：
[1] European Journal of Inorganic Chemistry, 2005, # 24, p. 5011 - 5017
[2] Tetrahedron, 1999, vol. 55, # 46, p. 13285 - 13300
[3] Tetrahedron, 2008, vol. 64, # 40, p. 9507 - 9514
[4] Journal of Organometallic Chemistry, 2009, vol. 694, # 9-10, p. 1473 - 1481
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Yield
Reaction Conditions
Operation in experiment
26%
With sodium hydrogencarbonate; sodium sulfate; triethylamine In dichloromethane; chloroform; water; acetonitrile
REFERENCE EXAMPLE 18 3-Morpholinobenzonitrile 3-Cyanophenol (1.77 g, 14.9 millimole) and triethylamine (6.30 ml, 45.2 millimole) were dissolved with methylene chloride (75 ml), and the solution is stirred under an argon gas environment at -10 degrees Celsius. The solution of trifluoroacetic andydride (3.79 ml, 22.5 millimole), dissolved with methylene chloride (15 ml), is dripped, and the mixture is stirred for 1.5 hours. After completion of the reaction, the solvent is removed under reduced pressure. A sodium hydrogencarbonate aqueous solution is added to the obtained concentrated residuum, and extraction is performed with methylene chloride. The organic layer is washed with a saturated saline solution, and dried using sodium sulfate. After the desiccant is separated through filtration, the filtrate is concentrated. The obtained concentrated residuum is purified using silica gel column chromatography (chloroform/methanol=100), and oily material is obtained. The obtained oily material is dissolved with acetonitrile (40 ml). Morpholine (33.0 ml, 378 millimole) is added to the solution, and the solution is stirred for 3 days while the solvent is refluxed. The solvent and the reagent which did not react were removed under reduced pressure. Water is added to the obtained concentrated residuum, and extraction is performed using chloroform. After the organic layer is dried (sodium sulfate), the desiccant is separated through filtration, and the filtrate is concentrated. The obtained concentrated residuum is purified using silica gel column chromatography (eluted with chloroform/hexane=1/2), and the subject compound is obtained as oily material (0.74 g, 26percent). 1H-NMR (CDCl3) δ (ppm): 3.15-3.19 (4H, m), 3.83-3.88 (4H, m), 7.09-7.18 (3H, m), 7.34 (1H, dd, J=7.6 Hz, 7.6 Hz).
26%
With sodium bicarbonate; triethylamine; trifluoroacetic anhydride In dichloromethane; water; acetonitrile
REFERENCE EXAMPLE 18 3-Morpholinobenzonitrile 3-Cyanophenol (1.77 g, 14.9mmol) and triethylamine (6.30 ml, 45.2 mmol) were dissolved in methylene chloride (75 ml) and stirred at -10° C. in an argon gas atmosphere. A solution of trifluoroacetic anhydride (3.79 ml, 22.5 mmol) dissolved in methylene chloride (15 ml) was added dropwise thereto, and after the addition was completed, the mixture was stirred for 1.5 hours. After the reaction was completed, the solvent was removed under reduced pressure, and an aqueous solution of sodium hydrogen carbonate was added to the resulting concentrated residue and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The drying agent was filtered off and the filtrate was concentrated. The resulting concentrated residue was purified by silica gel column chromatography (chloroform/methanol=100) to give oily substances. The resulting oily substances were dissolved in acetonitrile (40 ml). Morpholine (33.0 ml, 378 mmol) was added thereto and the mixture was stirred for 3 days under heating at reflux. The solvent and unreacted reagents were distilled off under reduced pressure, water was added to the concentrated residue, and the mixture was extracted with chloroform. The organic layer was dried (over sodium sulfate), the drying agent was filtered off, and the filtrate was concentrated. The resulting concentrated filtrate was purified by silica gel column chromatography (eluent: chloroform/hexane=1/2) to give the title compound (0.74 g, 26percent) as oily substances. 1 H-NMR (CDCl3) δ (ppm): 3.15-3.19(4H, m), 3.83-3.88(4H, m), 7.09-7.18(3H, m), 7.34(1H, dd, J=7.6 Hz, 7.6 Hz).
With sodium t-butanolate In toluene at 60℃; for 4h;
72%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90℃; for 20h;
54%
With sodium t-butanolate In toluene at 80℃; for 2h;
51%
With N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 3h; Electrochemical reaction;
40%
With copper(l) iodide; potassium carbonate; <i>L</i>-proline In dimethyl sulfoxide at 90℃; for 24h;
26.6%
With bis(η3-allyl-μ-chloropalladium(II)); [(μ-Ph2PCH2PPh2)Co2(CO)4(μ,η-Me2NCH2CCP(C6H11)2)]; sodium t-butanolate In toluene at 80℃; for 2h; Inert atmosphere;
A mixture of 119A (9.50 g) in 6N aqueous sulfuric acid (80 mL) was refluxed for 20 h. After cooling to to 0C, the mixture was brought to a pH of 2 by the slow addition of aqueous sodium hydroxide solution (50% w/w). After stirring for 15 min, the resulting solid was collected by filtration and washed with water then triturated with ethyl acetate (600 ml). The aqueous filtrate was extracted with additional ethyl acetate (450 ml) and the combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 9.50 g of 119B as a light pink solid. HPLC Ret. Time: 1.94 min. MH+ (m/z) 208.1.
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