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EXAMPLE II 2-Ethoxy-benzonitrile 25 g (210 mmol) of 2-hydroxylbenzonitrile are heated, together with 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide, in 500 ml of acetone under reflux overnight. The solid is filtered off, the solvent is removed in vacuo and the residue is distilled in vacuo. 30.0 g (97%) of a colorless liquid are obtained. 200 MHz 1H-NMR (DMSO-D6): 1.48, t, 3H; 4.15, quart., 2H; 6.99, dt, 2H; 7.51, dt, 2H.
With potassium carbonate; In acetone;
EXAMPLE 3A 2-Ethoxybenzonitrile 25 g (210 mmol) of 2-hydroxybenzonitrile are refluxed with 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide in 500 ml of acetone overnight. The solid is filtered off, the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. This gives 30.0 g (97%) of a colourless liquid. 200 MHz 1H-NMR (DMSO-d6): 1.48, t, 3H; 4.15, quart., 2H; 6.99, dt, 2H; 7.51, dt, 2H.
With potassium carbonate; In acetone;
EXAMPLE 11A 2-Ethoxy-benzonitrile 25 g (210 mmol) of 2-hydroxybenzonitrile, 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide in 500 ml of acetone are refluxed overnight. The solid is filtered off, the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. This gives 30.0 g (97%) of a colourless liquid. 200 MHz 1H-NMR (DMSO-d6): 1.48 (t, 3H); 4.15 (quart., 2H); 6.99 (dt, 2H); 7.51 (dt, 2H).
With potassium carbonate; In acetone;
EXAMPLE 12A 2-Ethoxybenzonitrile 25 g (210 mmol) of 2-hydroxybenzonitrile, 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide are refluxed in 500 ml of acetone overnight. The solid is filtered off, the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. This gives 30.0 g (97%) of a colorless liquid. 200 MHz 1H-NMR (DMSO-d6): 1.48 (t, 3H); 4.15 (quart., 2H); 6.99 (dt, 2H); 7.51 (dt, 2H).
Step S5A: Synthesis of 5-chloro-2-hydroxy-benzonitrile (5A) To a solution of 2-hydroxy-benzonitrile (5g, 42mmol) in chloroform (50mL) was added 15mL of a solution of NCS (N-chlorosuccinimide, 5.558g, 44.1mmol) in chloroform. The reaction mixture was refluxed overnight. TLC monitored the reaction. After the reaction completed, the mixture was poured into ice-water. The organic layer was washed with water, then stayed overnight. The precipitated solids were collected by filtration. The filtrate was concentrated, recrystallized from chloroform and filtered to give a solid. The two batches of product were combined to give 4g of 5-chloro-2-hydroxy-benzonitrile (5A). 1H-NMR (DMSO-d6) : delta (ppm): 11.44 (s, 1H), 7.77 (d, J = 2.4 Hz, 1H), 7.55 (dd, J1 = 8.8 Hz, J2 = 2.4 Hz, 1H), 7.02 (d, J = 9.2 Hz, 1H). MS (ESI): M++1=154.6.
4 g
With N-chloro-succinimide; In chloroform;Reflux;
Step S5A: Synthesis of 5-chloro-2-hydroxy-benzonitrile (5A) To a solution of 2-hydroxy-benzonitrile (5 g, 42 mmol) in chloroform (50 mL) was added 15 mL of a solution of NCS(N-chlorosuccinimide, 5.558 g, 44.1 mmol) in chloroform. The reaction mixture was refluxed overnight. TLC monitored the reaction. After the reaction completed, the mixture was poured into ice-water. The organic layer was washed with water, then stayed overnight. The precipitated solids were collected by filtration. The filtrate was concentrated, recrystallized from chloroform and filtered to give a solid. The two batches of product were combined to give 4 g of 5-chloro-2-hydroxy-benzonitrile (5A). 1H-NMR (DMSO-d6): delta (ppm): 11.44 (s, 1H), 7.77 (d, J=2.4 Hz, 1H), 7.55 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.02 (d, J=9.2 Hz, 1H). MS (ESI):
4-(3-aminobenzofuran-2-yl)quinoline-2(H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 5h;
General procedure: To a solution of <strong>[4876-10-2]4-bromomethylquinoline-2-one</strong> 1a [16a] or 1b [16b] (20.0 mmol) in DMF (25 mL) was added salicylonitrile 2 (2.38 g, 30.0 mmol) and anhydrous potassium carbonate (5.52 g,40.0 mmol). The mixture was heated at 100 °C for 5 h. After cooling to room temperature, then water (50 mL) was added and stirred for 20 min. The solid was filtered and recrystallized from HOAc to give 3.
To a 250 mL three-necked flask, 5.95 g (0.05 mol) of o-cyanophenol, 20 mL of 10% aqueous NaOH solution and 80 mL of toluene were separately added, and the mixture was heated to 70 C, and the reaction was kept at this temperature for 1 h. After 1 h, the temperature was lowered to 60 C, and 9.24 g of diethyl sulfate was slowly added dropwise.After the dropwise addition, the temperature was raised to 70 C and the reaction was continued for 2 h. The disappearance of o-cyanophenol was detected by TLC, and the mixture was cooled to separate liquid. The toluene layer was evaporated to give a pale yellow oily liquid, 2-ethoxybenzonitrile, 6.98 g, yield 95%.
93%
11.9 g (0.1 mol) of salicylic acid nitrile, 100 mL of toluene, and 48 g of 10% aqueous NaOH solution were sequentially added to a 250 mL four-necked flask under stirring.The temperature was raised to 68 C in a water bath, and the mixture was kept for 1 hour, and then 9.2 g (0.06 mol) of diethyl sulfate was added dropwise, and after the completion of the dropwise addition, the temperature was raised to 75 C, and the reaction was kept for 1 hour.The temperature was lowered to 68 C, and 9.2 g (0.06 mol) of diethyl sulfate was added dropwise. After the completion of the dropwise addition, the temperature was raised to 75 C, and the reaction was kept for 2 hours. The TLC tracking was carried out until the salicylonitrile was completely reflected.Cooling, liquid separation, collecting the organic layer, drying with anhydrous sodium sulfate, and then evaporating the toluene solvent,A yellowish oily liquid was obtained in an amount of 13.7 g, a yield of 93%, and a gas-mass spectrometric analysis content of 97%.
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