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Chemical Structure| 719-59-5 Chemical Structure| 719-59-5
Chemical Structure| 719-59-5

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Synonyms: 5-Chloro-2-aminobenzophenone

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Product Details of 2-Amino-5-chlorobenzophenone

CAS No. :719-59-5
Formula : C13H10ClNO
M.W : 231.68
SMILES Code : NC1=C(C=C(Cl)C=C1)C(=O)C1=CC=CC=C1
Synonyms :
5-Chloro-2-aminobenzophenone
MDL No. :MFCD00007839
InChI Key :ZUWXHHBROGLWNH-UHFFFAOYSA-N
Pubchem ID :12870

Safety of 2-Amino-5-chlorobenzophenone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501

Application In Synthesis of 2-Amino-5-chlorobenzophenone

* 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 [ 719-59-5 ]

[ 719-59-5 ] Synthesis Path-Downstream   1~20

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  • 2,4-dichloro-10-methylacridin-9-(10H)-one [ No CAS ]
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  • 2,4-dichloro-10-methylacridin-9-(10H)-one [ No CAS ]
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  • [ 35308-02-2 ]
  • 2,4-dichloro-10-methylacridin-9-(10H)-one [ No CAS ]
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  • 13
  • [ 36062-04-1 ]
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  • [ 1408335-44-3 ]
YieldReaction ConditionsOperation in experiment
95% With trifluoroacetic acid; at 100℃; for 0.666667h; General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2?3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60?80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below.#10;
  • 14
  • [ 32249-35-7 ]
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  • [ 121659-90-3 ]
YieldReaction ConditionsOperation in experiment
46% With ytterbium(III) triflate; In ethanol; at 20℃; In a 5 ml round-bottomed flask, (2-amino-5-chlorophenyl)(phenyl)methanone (100 mg, 432 ?????, Eq: 1.00) and <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (79.8 mg, 561 ?????, Eq: 1.3) were combined with EtOH (1.5 ml) to give a light yellow solution. Ytterbium triflate (26.9 mg, 43.2 ?????, Eq: 0.1) was added. The mixture was stirred at room temperature overnight, upon which a white precipitate formed. The precipitate was filtered and washed with ethanol to provide the title compound (67 mg, 46%) as a white powder.
46% With ytterbium(III) triflate; In ethanol; at 20℃; Step A: 6-Chloro-2-cyclopropyl-4-phenyl-quinoline-3-carboxylic acid methyl ester In a 5 ml round-bottomed flask, (2-amino-5-chlorophenyl)(phenyl)methanone (100 mg, 432 μmol, Eq: 1.00) and <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (79.8 mg, 561 μmol, Eq: 1.3) were combined with EtOH (1.5 ml) to give a light yellow solution. Ytterbium triflate (26.9 mg, 43.2 μmol, Eq: 0.1) was added. The mixture was stirred at room temperature overnight, upon which a white precipitate formed. The precipitate was filtered and washed with ethanol to provide the title compound (67 mg, 46%) as a white powder.
  • 15
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  • [ 74-88-4 ]
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  • 16
  • [ 16619-14-0 ]
  • [ 719-59-5 ]
  • C28H19ClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 60℃; for 24h;Inert atmosphere; General procedure: To a mixture of 2-aminobenzophenone (1.1mmol, 0.22g) and 2-phenyl-2,3-dihydroquinolin-4-one (1.1mmol, 0.25g) was added T3P® (2.2mmol, 0.70g) and the reaction mixture stirred at 60°C for 24h. Water (100mL) was added to dissolve T3P® and the mixture extracted with dichloromethane (3×60mL). The combined organic extracts were washed with brine, dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was recrystallized from methanol to give product 6a as yellow needles (57percent).
  • 17
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  • [ 616-38-6 ]
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YieldReaction ConditionsOperation in experiment
68% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1-methyl-pyrrolidin-2-one; at 250℃; for 0.2h;Flow reactor; General procedure: Selective N-monomethlyation reactions were performed in a Vapourtec E-series continuous flow system equipped with a high temperature tube reactor (10 mL, stainless steel, 0.03'' i.d., Fig. 2 ) and a membrane back pressure regulator (Zaiput). Stock solutions of aniline (20 mmol, 1.0 equiv, 2 M), DMC (5.05 mL, 60 mmol, 3.0 equiv, 6 M), and DBU (4.47 mL, 30 mmol, 1.5 equiv, 3 M) were prepared in oven-dried 10 mL volumetric flasks using NMP as the solvent. The solutions were transferred to screw-thread vials with septum caps and reagents were pumped directly from the vials. After the high temperature coiled tube reactor was heated to 250 °C, peristaltic pumps (Vapourtec V-3) were used to pump the reactant solutions into the system (0.277 mL/min each for a 12 min residence time). The solutions were mixed with a cross-mixer (0.4? i.d.), passed though the high temperature coiled tube reactor. Upon exiting the reactor, the reaction stream was passed through a short segment of stainless steel tubing to enable the reaction to cool and then exited the system by passage through the back pressure regulator (Note: PFA fittings should not be used at the exit of the reactor as they will deform due to the high temperature of the reaction stream and cause leaks in the system. Stainless steel connectors and tubing (12'') were used in our system.). After the flow system was equilibrated for 18 min, the product stream was collected for 5 min (2.77 mmol of aniline). The crude mixture was dissolved in ethyl acetate and washed with brine. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage 25 g Ultra-sil, 3?15percent ethyl acetate in hexanes) to afford the desired product.
  • 18
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  • [ 51997-51-4 ]
  • (2-((3-((9H-carbazol-4-yl)oxy)-2-hydroxypropyl)amino)-5-chlorophenyl) (phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In ethanol; for 24h;Reflux; General procedure: 5a (239 mg, 1 mmol), and 4-fluoroaniline (134 mg, 1.2 mmol)were added to ethanol and the resulting heterogeneous solutionwas reuxed for 24 h. The mixture was cooled to room temperatureand ltered through a pad of celite and the ltrate was concen-trated under reduced pressure. The residue was puried by ashchromatography on silica-gel with 20% ethyl acetate in hexane.Yielding 80% compound 10a (348 mg) as a white solid. Compounds10b-g were synthesized following the procedure of preparation10a.
  • 19
  • [ 50-00-0 ]
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  • [ 1022-13-5 ]
YieldReaction ConditionsOperation in experiment
92% With sulfuric acid; at 25 - 45℃; for 2.5h;Green chemistry; Take 59g of 2-amino-5-chlorobenzophenone and 180g of 98percent sulfuric acid, stir evenly at 25 ° C, and raise the temperature to 40 ~ 45 ° C, Add 42.3 g of paraformaldehyde in batches at this temperature(7.7g paraformaldehyde is added every 0.5h)After the addition, the reaction was allowed to stand for 2 hours, and the temperature was lowered to 20 ° C to obtain an N-methylation reaction solution, which was used. Take 280g of 25percent ammonia water and 240g of methanol to cool to below 10 °C, and start adding N-methylation reaction solution.Control the dropping temperature at 10 ~ 15 ° C, the dropping time is 1 ~ 2h, after the addition is completed,The temperature was raised to 65-70 ° C for 1 h, and then the temperature was lowered to 5 ° C or less. The crystal was filtered to obtain 70 g of crude 2-methylamino-5-chlorobenzophenone, and the crude product was added to 200 g of methanol to reflux.Then, the temperature was lowered to 10 ° C for suction filtration, and 400 g of water washing filter cake was dried at 60 ° C to obtain 57.6 g of 2-methylamino-5-chlorobenzophenone refined product, and the yield was 92percent.The product HPLC was 99.6percent, and the product IR was consistent with the standard spectrum of 2-methylamino-5-chlorobenzophenone.
  • 20
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  • [ 96516-29-9 ]
  • C20H11ClFN3O2 [ No CAS ]
 

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• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • 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 • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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