Name: 7463-31-2|3-Acetamidoacetophenone|98%
Brand: Ambeed
SKU: A110284
Rating: 91 (26 reviews)

1
[ 7463-31-2 ]
[ 108-24-7 ]
[ 79127-41-6 ]

Reference： [1]Journal of the Chemical Society,1945,p. 629

2
[ 108-24-7 ]
[ 99-03-6 ]
[ 7463-31-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane at 20℃; Inert atmosphere;
99%	With pyridine at 20℃; for 1h;
96.8%	In toluene at 20 - 55℃; for 1h;	1 Example 1; Preparation of N-(3-Acetylphenyl)acetamide To a suspension of 3' - aminoacetophenoe (50. 9 g, 377 mmol) in toluene (250 ml) was added dropwise acetic anhydride (39. 6 g, 388 mmol) at room temperature, and the mixture was kept at 55°C for one hour and then cooled to a temperature not more than 20°C. The crystals separated were filtered to give the objective compound (64.58 g ; 96. 8% yield) as a pale yellow powder.

95%	With zinc(II) oxide at 20℃; for 0.25h;
92%	Stage #1: acetic anhydride; 1-(3-aminophenyl)ethanone In ethyl acetate at 20℃; for 7h; Inert atmosphere; Stage #2: With potassium carbonate In ethyl acetate at 20℃; Inert atmosphere;
92%	With pyridine for 0.5h; Heating;
90%	In neat (no solvent) at 20℃; for 0.133333h;	Catalytic tests General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 °C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data.
88%	With ZnAl₂O₄ nanoparticles at 20℃; for 0.166667h; Neat (no solvent);
82.8%	With triethylamine In toluene at 20 - 40℃; for 2h;	2 Example 2; Preparation of N- (3-acetylphenyl) acetamide To a mixture of 3'-aminoacetophenone (10.0 g, 74.0 mmol), triethylamine (8. 98 g, 88.8 mmol) and toluene (50 ml) was added dropwise acetic anhydride (8.31 g, 81.4 mmol) at room temperature, and the mixture was kept at 30 to 40°C for 2 hours. The crystals separated were filtered at room temperature to give the objective compound (10.86 g; 82. 8% yield) as a pale yellow powder.
72%	at 0 - 70℃; Inert atmosphere;
	With acetic acid
	at 30℃; for 1h;	4.2.2.1 Acetylation 40mmol of the appropriated amine was added carefully over 50mL of ice cooled acetic anhydride to avoid the temperature surpasses 30°C. After 1h, 200mL of cold distilled water was added, and the precipitated was filtered out and recrystallized from 40mL of ethanol. Mean yield of approximately 60%.
	With dmap In dichloromethane at 20℃;
	With copper(ll) bromide In dichloromethane at 20℃;	9 4.1.5.9. N-(3-(2-((3-(methylthio)phenyl)amino)thiazol-4-yl)phenyl)acetamide (4 i). 1-(3-aminophenyl)ethanone (50 mg, 0.37 mmol) was dissolved in CH2Cl2 (600 ml) then acetic anhydride (42 ml, 0.45 mmol) was added. The reaction was stirred at room temperature upon completeness. The reaction mixture was washed with 0.1N sodium carbonate, the organic phase was concentrated in vacuum and resuspended in ethyl acetate (1 ml) and CuBr2 (99 mg, 0.3 mmol) was added. The mixture was then stirred at reflux overnight. The organic phase was washed with H2O (2 x 2 ml),concentrated to obtain 1-(3-aminophenyl)-2-bromoethanone. The bromoketone (64 mg, 0.3 mmol) was resuspended in anhydrous EtOH (1 ml) and conjugated with 1-(3-(methylthio)phenyl)thioureaa (59 mg, 0.3 mmol) as previously described. The final product was purified by preparative HPLC, the peak of interest was concentrated to obtain the title compound. (96 mg, 73%) 1H NMR (300 MHz, CDCl3) δ 7.95-7.89 (m 1H), 7.60-7.50 (d, J 7.7 Hz, 2H), 7.40-7.29 (m, 3H), 7.24 (t, J 8.0 Hz, 1H), 7.10 (ddd, J 8.1, 2.2, 0.8 Hz, 1H), 6.93 (ddd, J 7.81.6, 0.9 Hz, 1H), 6.83 (s, 1H), 2.43 (s, 3H), 2.17 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 168.5, 164.3, 150.7, 140.9, 140.3 ,138.3, 135.2, 129.8, 129.5, 122.1, 121.0, 119.6, 117.6, 115.7, 114.8, 102.7, 24.8, 15.7. ESI-MS m/z: 356.1 [M+H]+.
6.39 g	In toluene at 20 - 55℃; for 3h;	87 Reference Production Example 87 Reference Production Example 87 (0853) To a mixture of 50 mL of toluene and 6.76 g of 3-aminoacetophenone, 4.7 mL of acetic anhydride was added dropwise, followed by stirring at room temperature for 2 hours and further heating and stirring at 55°C for one hour. After cooling to room temperature, filtration, and washing with toluene, the obtained residue was dried under reduced pressure to obtain 6.39 g of N-(3-acetylphenyl)acetamide (C87A). 1H-NMR (CDCl3) δ (ppm): 8.00 (1H, s), 7.92 (1H, d, J = 8.2 Hz), 7.69 (1H, d, J = 7.8 Hz), 7.61 (1H, bs), 7.43 (1H, t, J = 7.9 Hz), 2.61 (3H, s), 2.22 (3H, s).
	at 20℃; for 2h;	33.a A) 3-Aminoacetophenone (50 g, 370 mmol) was dissolved in acetic anhydride (35 mL, 370 mmol) and stirred at room temperature for 2 hours. The acetic anhydride was evaporated under reduced pressure to give white crystals which were taken directly without further purification.
	In dichloromethane at 0 - 20℃; Inert atmosphere;
	With dmap In dichloromethane

Reference： [1]Zhao, Lele; Cao, Danyan; Chen, Tiantian; Wang, Yingqing; Miao, Zehong; Xu, Yechun; Chen, Wuyan; Wang, Xin; Li, Yanlian; Du, Zhiyan; Xiong, Bing; Li, Jian; Xu, Chunyan; Zhang, Naixia; He, Jianhua; Shen, Jingkang [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3833 - 3851]
[2]Shaikh, Ajam C.; Chen, Chinpiao [Journal of labelled compounds and radiopharmaceuticals, 2008, vol. 51, # 1, p. 72 - 76]
[3]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2004/87637, 2004, A1 Location in patent: Page 16
[4]Hosseini Sarvari, Mona; Sharghi, Hashem [Tetrahedron, 2005, vol. 61, # 46, p. 10903 - 10907]
[5]Location in patent: experimental part Temperini, Andrea; Terlizzi, Raffaella; Testaferri, Lorenzo; Tiecco, Marcello [Synthetic Communications, 2010, vol. 40, # 2, p. 295 - 302]
[6]Location in patent: experimental part Vogl, Michael; Kratzer, Regina; Nidetzky, Bernd; Brecker, Lothar [Organic and Biomolecular Chemistry, 2011, vol. 9, # 16, p. 5863 - 5870]
[7]Farhadi, Saeed; Jahanara, Kosar [Cuihua Xuebao/Chinese Journal of Catalysis, 2014, vol. 35, # 3, p. 368 - 375]
[8]Location in patent: scheme or table Farhadi, Saeid; Panahandehjoo, Somayeh [Applied Catalysis A: General, 2010, vol. 382, # 2, p. 293 - 302]
[9]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2004/87637, 2004, A1 Location in patent: Page 16
[10]Pialat, Amelie; Liegault, Benoit; Taillefer, Marc [Organic Letters, 2013, vol. 15, # 7, p. 1764 - 1767]
[11]Rupe; Braun; v. Zembrzuski [Chemische Berichte, 1901, vol. 34, p. 3522]
[12]Blau, Lorena; Menegon, Renato Farina; Trossini, Gustavo H. G.; Molino, João Vitor Dutra; Vital, Drielli Gomes; Cicarelli, Regina Maria Barretto; Passerini, Gabriela Duó; Bosquesi, Priscila Longhin; Chin, Chung Man [European Journal of Medicinal Chemistry, 2013, vol. 67, p. 142 - 151]
[13]Zhang, Yu-Juan; Shen, Liu-Lan; Cheon, Hyae-Gyeong; Xu, Yong-Nan; Jeong, Jin-Hyun [Archives of Pharmacal Research, 2014, vol. 37, # 5, p. 588 - 599]
[14]Pesce, Emanuela; Bellotti, Marta; Liessi, Nara; Guariento, Sara; Damonte, Gianluca; Cichero, Elena; Galatini, Andrea; Salis, Annalisa; Gianotti, Ambra; Pedemonte, Nicoletta; Zegarra-Moran, Olga; Fossa, Paola; Galietta, Luis J.V.; Millo, Enrico [European Journal of Medicinal Chemistry, 2015, vol. 99, p. 14 - 35]
[15]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - EP2927218, 2015, A1 Location in patent: Paragraph 0853
[16]Current Patent Assignee: Shanghai Institute of Materia Medica (in: CAS); CHINESE ACADEMY OF SCIENCES - CN103833671, 2016, B Location in patent: Paragraph 0129; 0130; 0131; 0132
[17]Ghosh, Chiranjit; Nagtilak, Prajyot Jayadev; Kapur, Manmohan [Organic Letters, 2019]
[18]Current Patent Assignee: SOUTHERN UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA - CN110627610, 2019, A Location in patent: Paragraph 0383

3
[ 99-03-6 ]
[ 75-36-5 ]
[ 7463-31-2 ]

Yield	Reaction Conditions	Operation in experiment
91%
70%	With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;
12%	In dichloromethane at 20℃; for 2h;

	With sodium hydroxide at 20℃;
	With triethylamine In N,N-dimethyl-formamide at 0℃; Inert atmosphere;	4.2.2 General procedure for the synthesis of 7a-n and 8a-i General procedure: (i) To a solution of aminoacetophenones (5.0 mmol) in anhydrous DMF (10 mL) were added 1.0 equiv of the corresponding acyl chloride (5.0 mmol) and 1.2 equiv of triethylamine (6.0 mmol) at 0 °C in ice-bath under argon atmosphere, and the reaction was allowed to stir until all the starting material had disappeared. Then, the resulting mixture was acidified with 1 M HCl to PH<7 and extracted with ethyl acetate (3 times). The obtained organic phase was washed with 5 % NaHCO3 (2 times) and brine (2 times), dried over Na2SO4 and concentrated in vacuo to give the intermediates 5a-n and 6a-i, which was used directly for the next step.
	With triethylamine In dichloromethane at 0 - 25℃; for 4h;
	With triethylamine In dichloromethane at 0 - 20℃; for 10h;

Reference： [1]El Sayed Aly, Mohamed Ramadan; Abd El Razek Fodah, Hamadah Hamadah; Saleh, Sherif Yousef [European Journal of Medicinal Chemistry, 2014, vol. 76, p. 517 - 530]
[2]Wang, Jingjing; Chen, Weiqiang; Zuo, Sujing; Liu, Lu; Zhang, Xinrui; Wang, Jianhui [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12334 - 12338][Angew. Chem., 2012, vol. 124, # 49, p. 12500 - 12504,5]
[3]Hooper, Julian; Watts, Paul [Journal of labelled compounds and radiopharmaceuticals, 2007, vol. 50, # 3, p. 189 - 196]
[4]Bandgar, Babasaheb P.; Adsul, Laxman K.; Chavan, Hemant V.; Shringare, Sadanand N.; Korbad, Balaji L.; Jalde, Shivkumar S.; Lonikar, Shrikant V.; Nile, Shivraj H.; Shirfule, Amol L. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 18, p. 5649 - 5657]
[5]You, Ao; Zhou, Jie; Song, Senchuan; Zhu, Guoxun; Song, Huacan; Yi, Wei [European Journal of Medicinal Chemistry, 2015, vol. 93, p. 255 - 262]
[6]Xiong, Xiaodong; Yeung, Ying-Yeung [Angewandte Chemie - International Edition, 2016, vol. 55, # 52, p. 16101 - 16105][Angew. Chem., 2016, vol. 128, # 52, p. 16335 - 16339,5]
[7]Chen, Yujie; Huang, Zhibin; Jiang, Yaqiqi; Shu, Sai; Yang, Shan; Shi, Da-Qing; Zhao, Yingsheng [Journal of Organic Chemistry, 2021, vol. 86, # 12, p. 8226 - 8235]

4
[ 7463-31-2 ]
[ 10202-87-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: nitric acid, acetic anhydride 2: KOH / ethanol; H₂O
	Multi-step reaction with 2 steps 1: nitric acid 2: aqueous hydrochloric acid
	Multi-step reaction with 2 steps 1: nitric acid 2: ethanolic sulfuric acid

Multi-step reaction with 2 steps 1: nitric acid / 0.25 h / 0 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 1 h / Reflux; Inert atmosphere

Reference： [1]Slama, James T.; Radziejewski, Czestaw; Oruganti, SubbaRao; Kaiser, E. T. [Journal of the American Chemical Society, 1984, vol. 106, # 22, p. 6778 - 6785]
[2]Leonard; Boyd [Journal of Organic Chemistry, 1946, vol. 11, p. 405,412]
[3]Waters [Journal of the Chemical Society, 1945, p. 629]
[4]Wang, Jingjing; Chen, Weiqiang; Zuo, Sujing; Liu, Lu; Zhang, Xinrui; Wang, Jianhui [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12334 - 12338][Angew. Chem., 2012, vol. 124, # 49, p. 12500 - 12504,5]

5
[ 7463-31-2 ]
[ 79127-41-6 ]

Reference： [1]Journal of the American Chemical Society,1984,vol. 106,p. 6778 - 6785
[2]European Journal of Medicinal Chemistry,2013,vol. 67,p. 142 - 151

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[ 7463-31-2 ]
[ 92642-29-0 ]