2-[4-(Diethylamino)-2-hydroxybenzoyl]benzoic acid

DryPowder

To a stirred solution of a compound '2' (1.0 equiv) in CH3-Diethylamino phenol(10.00 g, 60.52 mmol) and phthalic anhydride (8.96 g, 60.52 mmol) in toluene (50 mL) wererefluxed under nitrogen for 4 h. The mixture was cooled to 50-60oC. 50mL of 35percent NaOH (w/w)aqueous solution was added and then heated to 90oC for 6 h. The resulting mixture was pouredinto 200 g ice, acidified with concentrated HCl, and allowed to stand at room temperature for2 h. The suspension was filtered, and the solid was recrystallized from ethanol, then dried toafford the desired product (18.60 g) in a 98percent yield.1), 165 g (1.0 mol) of N, N-diethyl-m-aminophenol, 148g (1.0mol) of phthalic anhydride charged into the raw material mixing tank 2, and then open the valve on the tube II12 22, the upper part of the reaction tank 1 1 flows through the tube II12 into the originalWhen the required amount (300 mL) is reached, the valve 22 is closed so that 165 g (1.0 mol) of N, N-diethylM-aminophenol, 148 g (1.0 mol) of phthalic anhydride and 300 mL of toluene were charged in the raw material mixing tank 2 under stirringLine mixed evenly, dubbed about 350mL of the original material (as a solution); The original material was warmed to 60 heat reserve.2) to make the valve 24 on the connecting pipe I14 open;Open the high tank 1 out of the valve on the tube I11, the toluene in the high tank 1 by the injection tube I11 plunger pump 3Tubular reactor 4, so that the tubular reactor 4 is filled with toluene (314mL), then close the valve 21, the valve 24, The tubular reactor 4 is heated to 150 ° C;3) so that the valve 24 on the connecting pipe I14, the valve 25 on the connecting pipe II15 is in an open state;Open the raw material mixing tank 2 valve 13 on the pipe 13, the raw material mixing tank 2 is the raw material by the pipe 13 is plungerThe pump 3 was injected into the tubular reactor 4 at a flow rate of 2.6 mL / min for reaction, the reaction temperature was stabilized to 150 ° C, and the resultingThe reaction material into the reaction tank 6, through the control valve on the connecting pipe II15 25, so that the original into the tubular reactor 4The volume of the reaction material of the material overflowing the tubular reactor 4 is equal, so as to realize the continuous reaction;The control reaction time (ie, the residence time of the material in the tubular reactor 4) is 120 min;4), raw material mixing tank 2 after the original material is emptied (after injection), close the raw material mixing tank 2 valve 13 of the valveDoor 23; then open the valve on the tube I11 21, toluene in the upper tank 1 by a tube I11 by the plunger pump 3 injection tubeType reactor 4, at which time the reaction mass remaining in the tubular reactor 4 is completely overflowed into the reaction liquid tank 6 untilWhen the tubular reactor 4 was filled with toluene (314 mL), the valve 21 on the tube I11 was closed;5), the valve 25 on the connecting pipe II15 is closed, and the reaction mixture in the reaction liquid tank 6 is cooled to room temperature20 ) beating, stop stirring after beating. Open the reaction solution tank 6 on the valve 26, the reaction after coolingThe mixture flows out from the outlet tube of the reaction liquid storage tank 6 and is filtered. The filter cake is washed with n-butanol (about 100 ml) and dried (at 0.08 MPaDried under vacuum at 60 to constant weight) to give 301.5g of light yellow solid, with a yield of 96.3percent and a purity of> 99.5percent by HPLC.In this embodiment, all of R1 and R2 in the N, N-dialkyl-m-aminophenol represent ethyl, that is, N, N-dialkyl-m-aminobenzeneThe phenol is N, N-diethyl m-aminophenol, and the resulting benzophenone derivative is 2- [4 '- (N, N-diethyl) amino-2'-hydroxybenzeneFormyl] benzoic acid.To a constant pressure dropping funnel, Stirring and refluxing apparatus in a three-necked flask, 16.523 g (0.10 mol) of 3-N, N-diethylaminophenol and 22.218 g (0.15 mol) of phthalic anhydride were added, Heating and stirring, Heating up to 115 ° C, And keep the temperature unchanged, Until the material in the reactor after the slow release of the appropriate amount of toluene to disperse, And then continue to react.4h after the stop heating, After the reaction system was cooled to 60 ° C, Stirring slowly into the NaOH solution, So that its pH = 12, Then heated to 90 ° C, And incubation reaction 2h, Stop the reaction.After cooling, the contents of the reactor are poured into the appropriate amount of water to dissolve the solid matter, And then divided into toluene layer with a separatory funnel (as far as possible) to obtain an aqueous layer.The water layer in the rapid stirring by dropping dilute hydrochloric acid to solution pH = 4 stop dropping dilute hydrochloric acid, Filter, And washed several times with an aqueous solution of pH = 4 several times, To the filtrate to clarify colorless, The filter cake is dry.The dried cake was recrystallized from a solution of absolute ethanol: toluene = 1: 1, Yield 93.4percent1.48 g(10 mmol) of phtalic anhydride and 1.65 g (10 mmol) of3-diethylaminophenol in 50 ml of benzene were refluxed with mixing for9 hours. Then precipitate was collected by filtration and washed with10 ml of benzene. Yield: 2.8 g (90percent). Mp 210 °C(recrystallization from methanol); UV-Vis (ethanol): l100 g (0.6 mol) of m-hydroxy-N, N-diethylaniline (HDEA) 95 g (0.64 mol) of phthalic anhydride was added to 350 ml of xylene, refluxed for 3 hours, cooled to 5 , and 500 ml of methanol was added to precipitate a solid. The obtained solid was filtered and washed with water to obtain 158 g (yield: 83percent) of a light pink solid product. The purity of the product was 99percent.A mixture of 3-diethyl aminophenol (165g, lmol) and phthalic anhydride (148 g, lmol) in toluene (400 ml) was refluxed overnight, it was then cooled to RT and the solid material was collected by filtration and washed with cold methanol and air dried, product A was obtained as light purplish powder, 250 gram, ~80 yield.A mixture of 3-diethyl aminophenol (165 g, 1 mol) and phthalic anhydride (148 g, 1 mol) in toluene (400 ml) was refluxed overnight, it was then cooled to RT and the solid material was collected by filtration and washed with cold methanol and air dried, product A was obtained as light purplish powder, 250 gram, ~80percent yield.General procedure: A solution of 3-dimethylamino phenol or 3-diethylamino phenol (1.0equiv) and substituted phthalic anhydride (1.0equiv) in toluene was refluxed under NCompound 1 was synthesized according to the previously reported procedure (Scheme 1) [40]. A suspension of 3-diethylaminophenol (1.46 g, 10.6 mmol) and o-phthalic anhydride (1.57 g, 10.6 mmol) in toluene was refluxed for 20 h. The reaction solvent was removed under vacuo and the crude product was dissolved in CH

Intermediates

Molecular Weight:313.3
XLogP3:3.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:313.13140809
Monoisotopic Mass:313.13140809
Topological Polar Surface Area:77.8
Heavy Atom Count:23
Complexity:421
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes