2-Amino-5-chlorobenzophenone

yellow powder

Take 10.0g of intermediate (II) into a three-necked bottle.50ml ethanol, 4.8g iron powder, After refluxing for 0.5 h, 1 ml of sulfuric acid (6 mol/L) was added dropwise.After the completion of the dropwise addition, the reaction was refluxed for 1 h.After the reaction is completed, a NaOH solution is added to adjust the pH to 8, Cool down to 50 ° C, add 0.2g activated carbon, Reflux for 0.5h, Thermal filtration into the crystallization bottle, cooling and crystallization, Ethanol washing, drying to obtain intermediate (III) 9.60g, The yield is 95.1percent.The melting point is 96.3-98.2 °C.A, in a reaction vessel equipped with a stirrer, a reflux condenser, 5-chloro-3-phenyl-benzisoxazole 0.26 mol, the mass fraction of 30percent 2-bromo-5-fluoronitrobenzene solution 390ml, nickel chloride powder 0.46 mol, control the stirring speed at 190 rpm, raise the solution temperature to 78 °C, reflux reaction 120 min; B, adding 90percent of 4-chlorophenethylamine solution with a mass fraction of 21percent slowly add the ethylene glycol dimethyl ether solution with a mass fraction of 37percent adding time to control at 110min, continue to reflux reaction 5h. C, add the mass fraction of 27percent sodium bicarbonate solution 200ml, reduce the solution temperature to 16 °C, molecular sieve bleaching, filtration, the filtrate was concentrated, again lowering the solution temperature to 5 °C, the mass fraction of 70percent triethylamine solution washing, calcium oxide dehydrating agent dehydration, to give crystals of 2-amino-5-chlorobenzophenone 55.59 g, yield 92percent.1) Weigh 180 g of raw material 5-chloro-3-phenyl-2, 1-benzisoxazole into 1.5 L of anhydrous methanol and 1.5 L of acetonitrile, After stirring and dissolving, add 10g Pd/C catalyst with Pd content of 3percent, stir and mix to form material I, The flow rate of the slurry pump was adjusted so that the flow rate of the material I was 40.0 g/min and entered the preheating module of the microreactor. 2) Adjust the flow rate of the H2 gas flowmeter to 350ml/min, and directly enter the reaction module group and material I to undergo catalytic hydrogenation reaction without preheating.As shown in Figure 2, the molar ratio of 5-chloro-3-phenyl-2, 1-benzisoxazole to hydrogen is 1:1.2, the reaction temperature is 80°C, the residence time of the reaction is 35s, and the reaction pressure is 1.0Mpa; then enter the cooling module, cooling module temperature is 30 °C, Collect the reaction solution from the outlet of the cooling module, recover the catalyst by filtration, and recover the solvent by distillation under reduced pressure.The residue was recrystallized from 80percent ethanol solution to obtain the target product 2-amino-5-chlorobenzophenone, 168.96g, yield 92.79percent, purity 99.68percent.General procedure: Under a NGeneral procedure: A solution of 2-phenylindole (1a, 97 mg, 0.5 mmol) and CsIn the installation of a stirrer, thermometer, In the reaction vessel of the reflux condenser, 3.55 mol of benzamide (2) was added, Raise the temperature of the solution to 123 ° C, Dropping p-chloroaniline (3) 1.41mol, after adding slowly warming to 195 , Adding 5.9 mol of stannous chloride, Raise the temperature of the solution to 250 ° C, At this temperature for 4 h, Until no gas is generated, Reducing the solution temperature to 95 ° C, Add the mass fraction of 15percent potassium chloride solution 500ml, The solution temperature was raised to 130 ° C, After 4h, Pour out the water layer, After cooling the solution, Precipitation of dark suspended solids, The suspension was added to a 2.5 L mass fraction of 55percent phosphoric acid solution, Reflux 23h, After cooling, The solution was poured into a 1200 ml solution of 25percent sodium nitrate solution, Reduce the solution temperature to 8 ° C, Add the mass fraction of 85percent cyclohexane extraction, Cyclohexane layer by adding the mass fraction of 35percent sodium sulfite solution 300ml, 2.5kPa vacuum distillation, Add the mass fraction of 95percent acetonitrile extraction 7 times, Precipitation of solids, filter, Phosphorus pentoxide was dehydrated to give 297.68 g of 2-amino-5-chlorobenzophenone in yellow crystals in a yield of 91percent

A metabolite of Diazepam; it had a much weaker anticonvulsant effect.

Molecular Weight:231.68
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:231.0450916
Monoisotopic Mass:231.0450916
Topological Polar Surface Area:43.1
Heavy Atom Count:16
Complexity:250
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes