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CAS No. :20716-41-0 MDL No. :MFCD20486609
Formula : C9H9NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 211.17 Pubchem ID :-
Synonyms :

Safety of [ 20716-41-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20716-41-0 ]

* 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 [ 20716-41-0 ]

[ 20716-41-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 498-02-2 ]
  • [ 20716-41-0 ]
YieldReaction ConditionsOperation in experiment
92% With nitric acid; acetic acid at 0 - 20℃; for 3h;
91% With nitric acid; acetic acid at 0 - 20℃; for 3h; 1.1 (1) Synthesis of compound 2: Dissolve 8.3 g of 4-hydroxy-3-methoxyacetophenone (compound 1) in an acetic acid solvent, slowly add 4 mL of dilute nitric acid dropwise at 0°C, and stir for 3 hours at room temperature. After the completion of the reaction, the reaction solution was poured into ice water to separate out the precipitate, which was filtered and dried to obtain compound 2 with a yield of 91.0%.
90% With nitric acid In acetic acid at 20℃; for 4h; 4.1.1. Synthesis of intermediate 3 and 4 The synthesis method of intermediates 3 and 4 were totallyprepared as our previously reported method [22]. The commerciallyavailable material compound 1-(4-hydroxy-3-methoxyphenyl)ethan-1-one (1, 3.32 g, 20 mmol) was dissolvedwith 50 mL of AcOH, followed by adding 60% HNO3 (2 mL) andstirred at room temperature for 4 h. After the reaction wascompleted, which was monitored by thin layer chromatography(TLC), the ice was added to yield a large amount of yellow precipitation.The precipitation was filtered to obtain the product compound2 in the yield of 90% without further purification.To a suspension of compound 2 (2.11 g, 10 mmol) in 100 mL ofDMF, K2CO3 (3.45 g, 25 mmol) and tetrabutylammonium fluoride(2.61 g, 10 mmol) were in order added. The CH3I (2.13 g, 15 mmol)was added and the mixturewas stirred at 50 °C for 24 h. The reactionwas quenched by adding of icewater. Then, the mixturewas filteredand the obtained crude product was purified over silica gel (ethylacetate: petroleum 1:5) to obtain intermediate 3 as white solid.Yield 81%. 1H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.72 (s, 1H), 4.04(s, 3H), 4.01 (s, 3H), 2.63 (s, 3H).13C NMR (101 MHz, CDCl3) d 195.01,154.01, 146.47, 144.14, 132.11, 116.80, 114.32, 61.99, 56.51, 26.18.
83% With nitric acid; acetic acid for 0.5h; Preparation of 2-bromo-1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone (3) 10041] 1 -(4-Hydroxy-3-methoxy-5-nitrophenyl)ethanone((a) L. E. Kiss, H. S. Ferreira, L. Torrio, M. J. Bonifcio, P. N.Palma, P Soares-da-Silva, D. A. Learnmonth, J. Med. Chem.,2010, 53, 3396-3411; (b) X. Lu, S. Wan, J. Jiang, X. Jiang, W.Yang, P. Yu, L. Xu, Z. Zhang, G. Zhang, L. Shan, Y. Wang, Eur. J. Med. Chem., 2011, 46, 2691-2698). To a solution of 4'-hydroxy-3'-methoxyacetophenone (10 g; 60.2 mmol) in acetic acid (140 ml) at AT, 70% HNO3 is added (4.2 ml; 66.3 mmol). The reaction mixture is stirred for 30 min and the yellow crystals are filtered, washed with ether and dried to arrive at 1-(4-Hydroxy-3-methoxy-5-nitrophenyl)ethanone (10.5 g; 83%), mp 158-159° C. (lit. 159-161° C., ethanol, X. Lu, S. Wan, J. Jiang, X. Jiang, W. Yang, P. Yu, L. Xu, Z. Zhang, G. Zhang, L. Shan, Y. Wang, Eur. J. Med. Chem., 2011, 46, 2691-2698). 1H NMR (CDCl3; 300 MHz) δ (ppm) 11.09 (1H; s), 8.30 (1H; d; J=1.5 Hz); 7.75 (1H; d; J=1.5 Hz); 4.01 (3H; s); 2.62 (3H; s). 13C NMR (CDCl3; 75 MHz) δ (ppm) 194.9; 150.4; 150.1; 133.0; 128.3; 117.7; 115.3; 56.9; 26.0. IR (neat) vmax cm-1 3228; 3091; 2988; 2925; 1676; 1612; 1535; 1413; 1378; 1350; 1329; 1218; 1136; 1047; 869; 735; 709; HRMS (DE) (m/z) [M-H]- calculated for C9H8NO5 210.0402. obtained 210.0404.
83% With nitric acid; acetic acid at 20℃; for 0.5h;
80% With nitric acid; acetic acid at 20℃; for 0.5h; regioselective reaction;
78% With nitric acid In acetic acid for 3h; Cooling with ice; 1 Example 1: Synthesis of Compound Apo-NO2 Take apocynin (1.66g, 10mmol), add 10ml glacial acetic acid to dissolve, slowly add 67wt% concentrated nitric acid 1.5ml under ice bath, react for 30min, remove ice water, react at room temperature for 3h, add to the system after the reaction is over. Ice water was filtered under suction to give a yellow solid, which was crystallised from EtOAc (EtOAc) This compound is a known compound and is shown by mass spectrometry and nuclear magnetic spectroscopy to be consistent with the patterns described in the literature.
75% With nitric acid; acetic acid at 0 - 20℃; 5.4. 1-(4-Hydroxy-3-methoxy-5-nitrophenyl)ethanone (4) Apocynin 1 (20 g, 120 mmol), dissolved in glacial acetic acid (300 ml), was cooled to 0 °C in an ice bath with stirring on. Nitric acid (65%, 14 ml, 224 mmol) was then added slowly through a dropping funnel. The reaction mixture was maintained at room temperature for 2 h and was then poured into ice water (250 ml) with stirring on for 10 min. After 30 min of standing, the reaction mixture was filtered through a Buchner funnel and the residue was washed with water, which was recrystallized in 95% ethanol to afford 19.1 g (75% yield) of 4 as a yellow needle crystal, mp: 159-161 °C. 1H NMR (CDCl3, 400 MHz): 11.13 (s, 1H, OH), 8.31 (d, 1H, J = 1.6 Hz, ArH), 7.77-7.76 (d, 1H, J = 1.6 Hz, ArH), 4.01 (s, 3H, OCH3), 2.63 (s, 3H, CH3CO). MS (ESI) m/z 212 [M + H]+. Analysis calculated for C9H9NO5·0.2H2O: C, 50.33; H, 4.41; N, 6.52. Found: C, 50.63; H, 4.23; N, 6.26.
55% With nitric acid; acetic acid at 20℃;
With diethyl ether; water; nitric acid; sodium nitrite
With nitric acid
24.0 g (75%) With nitric acid In water 18 4'-Hydroxy-3'-methoxy-5'-nitroacetophenone EXAMPLE 18 4'-Hydroxy-3'-methoxy-5'-nitroacetophenone To a solution containing 40 ml of nitric acid (d=1.41) and 40 ml of water was gradually added while cooling (below 7° C.) and stirring 25.0 g of 4'-hydroxy-3'-methoxyacetophenone. After stirring for 0.5 h at 0° C. the product was filtered, washed first with diluted nitric acid (1:1) and then with water. Yield 24.0 g (75%). The 1 H-NMR-spectrum of the product was in accordance with the structure alleged.
Stage #1: 1-(3-methoxy-4-hydroxyphenyl)ethanone With sulfuric acid In acetic acid at 5 - 10℃; for 0.166667h; Stage #2: With nitric acid In acetic acid at 20℃; for 2h;
With nitric acid; acetic acid In water at 20℃; for 3h;

Reference: [1]Zhang, Shun; An, Baijiao; Li, Jiayan; Hu, Jinhui; Huang, Ling; Li, Xingshu; Chan, Albert S. C. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7404 - 7410]
[2]Current Patent Assignee: INST OF ZOOLOGY GUANGDONG ACADEMY OF SCIENCES - CN112939989, 2021, A Location in patent: Paragraph 0044-0047
[3]Yan, Jun; Xu, Yuzhu; Jin, Xing; Zhang, Qiaoxuan; Ouyang, Feng; Han, Liqiao; Zhan, Min; Li, Xingshu; Liang, Baoxia; Huang, Xianzhang [European Journal of Medicinal Chemistry, 2022, vol. 227]
[4]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US2015/344460, 2015, A1 Location in patent: Paragraph 0041; 0042; 0043
[5]Egorov, Maxim; Delpech, Bernard; Aubert, Genevieve; Cresteil, Thierry; Garcia-Alvarez, Maria Concepcion; Collin, Pascal; Marazano, Christian [Organic and Biomolecular Chemistry, 2014, vol. 12, # 9, p. 1518 - 1524]
[6]Location in patent: experimental part Kiss, László E.; Ferreira, Humberto S.; Torrão, Leonel; Bonifácio, Maria João; Palma, P. Nuno; Soares-Da-Silva, Patrício; Learmonth, David A. [Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3396 - 3411]
[7]Current Patent Assignee: JINAN UNIVERSITY (GUANGZHOU) - CN108947859, 2018, A Location in patent: Paragraph 0085-0086
[8]Location in patent: experimental part Lu, Xiaoyu; Wan, Sainan; Jiang, Jie; Jiang, Xiaojian; Yang, Wenjing; Yu, Pei; Xu, Lipeng; Zhang, Zaijun; Zhang, Gaoxiao; Shan, Luchen; Wang, Yuqiang [European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2691 - 2698]
[9]Hitge, Rialette; Petzer, Jacobus P.; Smit, Sharissa; Petzer, Anél [Bioorganic and medicinal chemistry letters, 2020, vol. 30, # 12]
[10]Anderson [Suomen Kemistiseuran Tiedonantoja, 1957, vol. 66, p. 1,5]
[11]Baeckstroem, Reijo; Honkanen, Erkki; Pippuri, Aino; Kairisalo, Pekka; Pystynen, Jarmo; et al. [Journal of Medicinal Chemistry, 1989, vol. 32, # 4, p. 841 - 846]
[12]Current Patent Assignee: ORION OYJ - US4963590, 1990, A
[13]Rana, Dharmarajsinh N.; Chhabria, Mahesh T.; Shah, Nisha K.; Brahmkshatriya, Pathik S. [Medicinal Chemistry Research, 2014, vol. 23, # 1, p. 370 - 381]
[14]Ren, Yichang; Wang, Yuxi; Li, Gang; Zhang, Zherong; Ma, Lingling; Cheng, Binbin; Chen, Jianjun [Journal of Medicinal Chemistry, 2021, vol. 64, # 8, p. 4498 - 4515]
  • 3
  • [ 20716-41-0 ]
  • [ 77-78-1 ]
  • [ 134610-32-5 ]
  • 4
  • [ 20716-41-0 ]
  • [ 74-88-4 ]
  • [ 134610-32-5 ]
YieldReaction ConditionsOperation in experiment
81% With tetrabutyl ammonium fluoride; potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; 4.1.1. Synthesis of intermediate 3 and 4 The synthesis method of intermediates 3 and 4 were totallyprepared as our previously reported method [22]. The commerciallyavailable material compound 1-(4-hydroxy-3-methoxyphenyl)ethan-1-one (1, 3.32 g, 20 mmol) was dissolvedwith 50 mL of AcOH, followed by adding 60% HNO3 (2 mL) andstirred at room temperature for 4 h. After the reaction wascompleted, which was monitored by thin layer chromatography(TLC), the ice was added to yield a large amount of yellow precipitation.The precipitation was filtered to obtain the product compound2 in the yield of 90% without further purification.To a suspension of compound 2 (2.11 g, 10 mmol) in 100 mL ofDMF, K2CO3 (3.45 g, 25 mmol) and tetrabutylammonium fluoride(2.61 g, 10 mmol) were in order added. The CH3I (2.13 g, 15 mmol)was added and the mixturewas stirred at 50 °C for 24 h. The reactionwas quenched by adding of icewater. Then, the mixturewas filteredand the obtained crude product was purified over silica gel (ethylacetate: petroleum 1:5) to obtain intermediate 3 as white solid.Yield 81%. 1H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.72 (s, 1H), 4.04(s, 3H), 4.01 (s, 3H), 2.63 (s, 3H).13C NMR (101 MHz, CDCl3) d 195.01,154.01, 146.47, 144.14, 132.11, 116.80, 114.32, 61.99, 56.51, 26.18.
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