3-Amino-2-cyclohexen-1-one

Dark yellow crystal

The 1, 3-cyclohexanedione (0 · 03mol) and ammonium acetate (0 · 039mol) added to 100ml three-necked flask, stir hook, the reaction conditions in an oil bath at 110 °C 15min, Remove the oil bath and then naturally cool, During which the reaction liquid is solidified. After cooling to room temperature, ethyl acetate (10 ml) is added, heated to dissolve and cooled to 0 °C., filtered and the filter cake is dried to obtain yellow crystals of 3-amino-2-cyclohexenone (Yield 93.6percent)Example 5A mixture of cyclohexane-1, 3-dione (56.1 g, 0.5 mol) and AcONHTo a 1 L two-necked flask charged 200 g (1.78 moL) of 1, 3-cyclohexanedione and 600 mL benzene, attached a Dean-Stark apparatus with a condenser and an ammonia inlet. The mixture was heated to reflux and ammonia gas was bubbling into the reaction. The water generated from the reaction was trapped in the Dean-Stark apparatus. The mixture formed two layers and the bottom layer was solidified after refluxing for 4 h. The reaction was then stopped and cooled down to room temperature. The benzene was decanted and the remaining solid was triturated with 300 mL chloroform and filtered to give the desired product as a yellow solid (167.1 g, 1.51 moL, 86percent).1HNMR (400 MHz, CDCl3): 5.23 (s, 1 H), 3.20 (bs, 1 H), 2.37 (m, 2 H), 2.28 (m, 2 H), 1.97 (m, 2 H).S1. At room temperature (25 ° C - 30 ° C), weigh 112g into 2240mL of absolute ethanol, 84.8g of anhydrous ammonium acetate, heated to 80 ° C, reflux for 3h, nitrogen protection.When no raw materials were monitored by S2.TLC, the temperature was lowered to room temperature, and 212 g of anhydrous sodium carbonate was added to react overnight.S3. The reaction mixture was filtered through Celite, and then filtered and evaporated to dryness to give a yellow solid, and the yellow solid was beaten with 100 mL of EA until the impurities were washed.S4. After beating, filter, the filtrate is dissolved in 2240 mL of absolute ethanol, and the solvent is removed by using a 200-300 mesh silica gel column which has been saturated with ethanol.The filtrate by rotary evaporation to give a yellow solid 89g, molar yield 80percent, TLC purity 96percent.Cyclohexane-1, 3-dione (22.42 g, 200 mmol, 1 eq) was dissolved in 250 ml dry toluene and ammonium acetate (14.42 g, 200 mmol, 1 eq) was added. After refluxing under Dean-Stark conditions for 4 hours, the reaction mixture was evaporated. After recrystallization in ethyl acetate, 7.78 g of pure end product was obtained as a yellow-orange powder.Preparation 1 Example 983-((6-Aminopyridin-2-yl)ethynyl)-7, 8-dihydroquinolin-5(6H)-one[00286] A mixture of cyclohexane-1 , 3-dione (30.0 g, 0.27 mol), ammonium acetate (44.49 g, 0.54 mol), and acetic acid (1 mL) in benzene (300 mL) is stirred at reflux for 7 h using a Dean-Stark trap, cooled down to r.t., concentrated at reduced pressure, and diluted with EtOH. The mixture is neutralized by means of NaHC0General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), aryl or alkyl amine (1.0 mmol), Cu(OAc)2 (8 molpercent) and TBHP (4.0 mmol, 0.56 mL of a 70percent aqueous solution) in water (0.5 mL) was stirred at 30 °C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/ petroleum ether (60-80 °C)].Into a 500 mL round bottom flask fitted with a Dean-Stark trap and a magnetic stirrer was added 150 mL of anhydrous benzene, 1, 3-cyclohexanedione (5.6 g, 0.05 mol), and ammonium acetate (7.7 g, 0.1 mol). The mixture was stirred continuously, and refluxed for 5 h. The reaction was allowed to reach room temperature. The precipitate was recrystallized with ethyl acetate to afford yellow crystals (1.73 g, 31percent yield). Mp-128-131 °C [lit. 128-131 °C (35)].

Molecular Weight:111.14
XLogP3:-0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:111.068413911
Monoisotopic Mass:111.068413911
Topological Polar Surface Area:43.1
Heavy Atom Count:8
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes