* 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 Acetaldehyde oxime; In methanol; at 65℃; for 4h;
General procedure: A typical reaction was carried out in a 10 mL flask. Benzonitrile (2 mmol), CuII-4 A (0.2 g), acetaldoxime (6 mmol) and MeOH (4 mL) were stirred at 65 C for 4 h. The solid was filtered, washed with MeOH and the filtrate evaporated. The residue was subjected to GC-MS analysis and NMR spectroscopy. The filtered catalyst can be recycled after drying at about 150 C for 1 h.
96%
With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; water; 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantyl chloride; for 1h;Schlenk technique; Reflux; Green chemistry;Catalytic behavior;
General procedure: In a Schlenk-tube of approximately 12 mL volume, 0.05 mmol Ru(II)-precursor (1, 2 or RuCl3×3H2O) and 0.15 mmol phosphine ligand were dissolved in 3 mL water. This was followed by addition of 1 mmol nitrile. The tube was equipped with a reflux condenser and then immersed to an oil bath of 108-110 C temperature. The reaction mixture was stirred magnetically under reflux on air. In case of aliphatic nitriles heavy-walled closed reaction tubes of 5 mL volume were used. At the end of the reaction (or at other appropriate reaction times) 50 muL samples were withdrawn from the hot reaction mixture and these were extracted with 3×2 mL dichloromethane. A 1.5 mL portion of the combined organic phases was passed through a plug of unhydrous MgSO4 and the resulting clear solution was analysed by gas chromatography.
90%
With sodium azide; water; at 90℃; for 8h;
General procedure: To an aqueous mixture of nitrile (1 mmol) in water (7 mL) was added NaN3 (0.1 mmol, 0.0065 g), then the reaction mixture was stirred vigorously in an oil bath preset at 90 C for the appropriate time as mentioned in Table 1. After completion of the reaction (monitoredby TLC), the reaction mixture was cooled and the precipitated-outsolid was filtered and washed with water (3 × 5 mL) to give the pure product. The products were identified by their 1H NMR spectra and their physical data (m.p.) were compared with those described in the literature. Spectral data for the selected compound are as follows.
80%
With water; In ethanol; at 50 - 60℃; for 2.5h;
General procedure: Amberlyst A26 OH (0.11 g) was added to a suspension ofthe nitrile (1 mmol) in EtOH-H2O (0.5 mL). The reactionmixture was stirred at 50-60 C, and the progress of thereaction was followed by TLC. After the completion ofreaction, the mixture was diluted with acetone or EtOAc andfiltered to remove the catalyst. The desired products wereisolated by evaporation of the EtOAc or addition of H2O and filtration of the precipitate.
General procedure: Benzyl cyanide (5 g, 42.7 mmol) was added slowly to concentrated sulfuric acid (20 ml) cooled by water-ice bath. The solution was stirred overnight. The reaction mixture was poured into ice water and neutralized with 20% NaOH. The aqueous phase was extracted by ethyl acetate (3*15 mL). The combined organic layers were washed with water (3*10 mL) and brine (3*10 mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate and hexane to give the title compound (4.5 g, 78%). 1H NMR (400 MHz, DMSO-d6) 7.54 (s, 1H), 7.20-7.32 (m, 5H), 6.87 (s, 1H), 3.38 (s, 2H).
Example 96 In analogy to example 64, on reaction of (S)-4-(3-ethoxy-pyrrolidin-1-yl)-7-iodo-2-methyl-quinoline hydrochloride, product of example 87b), with <strong>[20101-92-2](4-chlorophenyl)-acetamide</strong> there was obtained: (S)-2-(4-chloro-phenyl)-N-[4-(3-ethoxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-yl]-acetamide as a light brown solid. ISP mass spectrum, m/e: 424.5 (M+1 calculated for C24H26N3O2Cl: 424).
With sodium hydroxide; methylamine hydrochloride; In N-methyl-acetamide; methanol; chloroform;
EXAMPLE 1 1-methyl-5-(4-chlorophenyl)-4(1H)-pyrimidinone A 4.2 g. portion of <strong>[20101-92-2]4-chlorophenylacetamide</strong> was mixed with 6 g. of dimethylformamide dimethyl acetal in 50 ml. of dimethylformamide. The mixture was stirred at 110 C. for about 6 hours in an open flask and was then allowed to cool to room temperature. The reaction mixture was poured over ice, and the precipitated product was separated by filtration and recrystallized from benzene-hexane. The purified intermediate, p-chloro-beta-dimethylamino-N-[(dimethylamino)methylene]atropamide, m.p. 155-156 C., was obtained in a yield of 2 g. A 1.2 g. portion of the above intermediate was dissolved in 75 ml. of methanol and 3 g. of methylamine hydrochloride was added. The mixture was stirred at reflux temperature while methylamine was bubbled in. After 1 hour, the mixture was evaporated to dryness, and the residue was taken up in hot ethyl acetate, which was then evaporated to 1/5 of its volume. The product spontaneously crystallized and was separated by filtration. The solids were dissolved in 100 ml. of chloroform, 1 cc. of 1N sodium hydroxide was added, and the solution was stirred for 15 minutes and dried over sodium bicarbonate. The chloroform was evaporated under vacuum, and the product was recrystallized from hot benzene to obtain 0.6 g. of 1-methyl-5-(4-chlorophenyl)-4(1H)-pyrimidinone, m.p. 220-221 C.
General Procedure for the synthesis of imides: 1 mmol of Tf2O (0.16 mL) was added to 1 mmol of ionic liquid at 0 C, and the mixture was stirred for 5 min at room temperature. Then, 1 mmol of the nitrile was added and the mixture was heated at 60 C. After 1 h, NaHCO3 (2%, 5 mL) was added and the mixture was extracted with EtOAc (2 × 5 mL). The organic layer was dried over Na2SO4 and evaporated. The crude product was purified by column chromatography using EtOAc/n-hexane (2:8) as eluent to afford the desired imide. Spectral and analytical data for new compounds:
General Procedure for the synthesis of imides: 1 mmol of Tf2O (0.16 mL) was added to 1 mmol of ionic liquid at 0 C, and the mixture was stirred for 5 min at room temperature. Then, 1 mmol of the nitrile was added and the mixture was heated at 60 C. After 1 h, NaHCO3 (2%, 5 mL) was added and the mixture was extracted with EtOAc (2 × 5 mL). The organic layer was dried over Na2SO4 and evaporated. The crude product was purified by column chromatography using EtOAc/n-hexane (2:8) as eluent to afford the desired imide. Spectral and analytical data for new compounds:
General Procedure for the synthesis of imides: 1 mmol of Tf2O (0.16 mL) was added to 1 mmol of ionic liquid at 0 C, and the mixture was stirred for 5 min at room temperature. Then, 1 mmol of the nitrile was added and the mixture was heated at 60 C. After 1 h, NaHCO3 (2%, 5 mL) was added and the mixture was extracted with EtOAc (2 × 5 mL). The organic layer was dried over Na2SO4 and evaporated. The crude product was purified by column chromatography using EtOAc/n-hexane (2:8) as eluent to afford the desired imide. Spectral and analytical data for new compounds:
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
