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Chemical Structure| 120578-03-2 Chemical Structure| 120578-03-2

Structure of 120578-03-2

Chemical Structure| 120578-03-2

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Product Details of [ 120578-03-2 ]

CAS No. :120578-03-2
Formula : C18H12ClNO
M.W : 293.75
SMILES Code : O=CC1=CC=CC(/C=C/C2=NC3=CC(Cl)=CC=C3C=C2)=C1
MDL No. :MFCD02684215
InChI Key :JTRDWIOIDMLMNN-XBXARRHUSA-N
Pubchem ID :10017305

Safety of [ 120578-03-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 120578-03-2 ]

* 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.

  • Downstream synthetic route of [ 120578-03-2 ]

[ 120578-03-2 ] Synthesis Path-Downstream   1~4

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  • [ 1826-67-1 ]
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YieldReaction ConditionsOperation in experiment
EXAMPLE 11 : PREPARATION OF 2-(3-(3-[2-(7-CHLORO-QUINOLIN^-YL)-VINYL]- PHENYL}-3-OXO-PROPYL)-BENZOIC ACID METHYL ESTER OF FORMULA XII:Toluene (500 ml), 3-[2-(7-chloro-quinolin-2-yl)-vinyl] benzaldehyde (50 g) were taken into a round bottom flask and stirred for about 10 minutes. The reaction mass was then cooled to 0 to -10 0C. Then Vinyl Magnesium bromide (1 M solution in THF) (230 ml) was added slowly at about 0 to -100C under nitrogen atmosphere. After the addition was complete, the reaction mass was maintained at 0 to -100C for about 2 hours. After the reaction was completed, the reaction mass was quenched with 10 % aqueous acetic acid solution (300 ml) below 10 0C . Toluene (250 ml) was then added to the reaction mass, and the temperature of the reaction mass was raised to 25-35 0C and stirred for about 30-45 minutes. The organic layer was separated and the aqueous layer was extracted with toluene (150 ml). The combined organic layer was washed with 5 % aqueous sodium bicarbonate solution (250 ml) followed by washing with water (2X400 ml). The organic layer was distilled azeotropically to remove the traces of water until the reaction volume was 400 ml and then cooled to 25-35 0C. Methyl 2-iodo benzoate (22.4 ml), THF (25 ml) and triethylamine (65.1 ml) was added to the residual organic layer. Palladium acetate (0.25 g) was added and the reaction mass was heated to reflux and maintained under reflux for about 24 hrs. After the reaction was completed, EPO <DP n="33"/>the reaction mass was filtered under hot condition and washed the filtered bed with toluene (100 ml). The combined filtrate was washed with water (2 X250 ml) under hot condition (60-70 0C). The toluene layer was Distill off completely under vacuum below 600C. Then toluene (75 ml) was added to the reaction mass and heated to 70-80 0C to get the clear dissolution. The solution was then cooled to about 25-35 0C and maintained for about 2 hours. Then the reaction mass was further cooled to 0-5 0C and stirred for about 4 hours. The separated solid was filtered and washed with chilled toluene (25 ml) and finally washed with hexanes (100 ml). The wet compound was dried at 50-550C under vacuum to afford 45 g of the title compound.
In a 2 ltr 4-necked flask equipped with a thermometer and mechanical stirrer, (400 g, 0.40 moles) vinyl magnesium bromide (I M solution in THF) was added in a solution of [E]-3-[2- (7- chloro-2-quinolinyl) ethenyl]-Benzaldehyde (100 g, 0.34 moles) in toluene (700 ml) and tetrahydrofuran (200 ml) at -40 0C (+/-5 0C). Stir the reaction mass for 2-4 hrs at -40 0C (+/-5 0C) and quench the reaction mass in 10% ammonium chloride solution ( 1 ltr). Organic layer washed with water then with 10%sodium chloride solution. Recover the solvent under vacuum to get moisture content NMT 0.05% and proceed to next stage immediately
EXAMPLE 9: Preparation of [E]-l-[3-[2-(7-ChIoro-2-quinolinyI)ethenyl]phenyl]-2-propen-l-ol (II): To a cooled (-10 to 0 C) and stirred suspension of [E]-3-2-(7-Chloro-2-quinolinyl)ethenyl]benzaldehyde (I) (lOOg, 0.34 mol) in tetrahydrofuran (300 mL) and toluene (1000 mL) in a 3.0 lt/4 neck round bottomed flask fitted with a mechanical stirrer, thermometer pocket and calcium chloride drying tube under nitrogen gas atmosphere, vinylmagnesium bromide (500 g, , approx. 1.0 molar solution in THF) was added drop wise60 minutes keeping the temperature to -10 to 0 C. The reaction mixture was stirred at -15 to + 20 C and progress of the reaction was monitored by TLC. After the reaction was(approx 2 hours), ammonium acetate (600 mL, 10% aqueous solution) was added to reaction mixture and the reaction mixture was stirred for 30 minutes. The toluene layer was separated and the aqueous layer was extracted with toluene (2 x 1000 mL), the toluene layers were combined, washed with water (2x1000 mL), driedsodium sulfate and evaporated under vacuum at 55 to 60 C to afford crude residue of [E]-l-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-2-propen-l-ol (II) which is used as such in the next stage. Yield 126 g. Purity (HPLC) =92.5 %
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YieldReaction ConditionsOperation in experiment
91% In tetrahydrofuran; ethylbenzene; at -15℃; A flask was charged with monoaldehyde, (£)-3-(2-(7-chloroquinolin-2- yl)vinyl)benzaldehyde III, (94.7 g), ethylbenzene (500 mL) and THF (200 mL), and stirred. The mixture was cooled to -15C. Vinyl magnesium chloride (1.6 M in THF, 232 mL) was slowly charged via additional funnel. Quench solution preparation: A flask was charged with Ammonium acetate (74.6 g), water (530 mL), solka flock (16.7g), ethylbenzene (60mL) and THF (20mL) and cooled to 5C. The batch was added into the quench solution. After quenching, the batch was warmed up and agitated at room temp. The batch was filtered, rinsed with ethylbenzene/THF and phase cut. The organic phase was washed with water. Solvent was removed under reduced pressure at ~50C. The batch was concentrated and slowly cooled to room temp and agitated for 15h. The crystalline product was collected by filtration, rinsed with ethylbenzene and dried under vacuum with nitrogen sweep to yield vinyl alcohol IV (94.94 g, 91% yield from the monoaldehyde III, (£)-3-(2-(7-chloroquinolin-2-yl)vinyl)benzaldehyde). 1NMR (500MHz, CDCl3) delta 8.10 (d, J= 8.5 Hz, IH), 8.08 (d, J= 2.0 Hz, IH), 7.71 (od, J= 16.2 Hz IH), 7.70 (d, J= 8.6 Hz, IH), 7.68 (m, IH), 7.64 (d, J= 8.5 Hz, IH), 7.55 (m, IH), 7.45 (dd, J= 8.6, 2.0 Hz, IH), 7.40 (t, J= 7.5 Hz, IH), 7.38 (od, J= 16.2 Hz, IH), 7.36 (om, IH), 6.09 (ddd, J= 17.1, 10.4, 5.9 Hz, IH), 5.41 (dt, J= 17.1, 1.3 Hz IH), 5.28 (brm, IH), 5.25 (m, IH) 2.23 (s, IH). 13C NMR (125MHz, CDCl3) delta 156.8, 148.6, 143.2, 140.1, 136.6, 136.1, 135.6, 135.0, 129.0, 128.8, 128.6, 128.2, 127.1, 126.85, 126.79, 125.7, 125.1, 1 19.6, 115.5, 75.2.
Example 1: Synthesis of 1-[(E)-3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl]-2-propen-1-ol; A suspension of (E)-3-(2-(7-chloro-2-quinolinyl)ethenyl)benzaldehyde (50 g, 0.17 mol, commercially available from Unibest Industrial Ltd., Ningbo, China) in 400 mL toluene was degassed at 0 C. A 1.6 M solution of vinylmagnesium chloride in THF (115 mL, 0.18 mol) was added dropwise over 30 minutes while keeping the internal temperature at <10 C. After stirring for 1 hour at 0-5 C, the reaction mixture was quenched by slow addition of 400 mL aqueous ammonium acetate solution (10 %). The two-phase mixture thus obtained was stirred for 1 hour to ensure the solvolysis of the magnesium salts. The separated organic layer was washed two times with 500 mL water and concentrated in vacuum to a volume of 75 mL. Then, again 75 mL acetonitrile were added and the mixture was concentrated in vacuum to 75 mL. After repetition of the last procedure, the resulting slurry was directly used in the next step.
 

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• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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