Alternatived Products of [ 2788-74-1 ]
Product Details of [ 2788-74-1 ]
CAS No. : | 2788-74-1 |
MDL No. : | MFCD00546760 |
Formula : |
C9H10N2O4
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
210.19
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 2788-74-1 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 2788-74-1 ]
* 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 [ 2788-74-1 ]
Yield | Reaction Conditions | Operation in experiment |
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87.A A.
A. Preparation of 4-ethylamino-3-nitrobenzoic Acid Methyl Ester In a manner similar to Example 31, 4-fluoro-3-nitrobenzoic acid was treated with ethylamine to give 4-ethylamino-3-nitrobenzoic acid, which was then esterified with anhydrous hydrogen chloride in methanol to give the title compound. 1H-NMR (CDCl3): δ 8.89 (1H, d), 8.28 (1H, br s), 8.06 (1H, dd), 6.87 (1H, d), 3.90 (3H, s), 3.42 (2H, m), 1.40 (3H, t). |
- 2
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[ 75-04-7 ]
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[ 96-99-1 ]
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[ 2788-74-1 ]
Yield | Reaction Conditions | Operation in experiment |
100% |
In water at 80℃; for 5h; |
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99% |
at 70℃; for 5h; |
4.2.2. General procedure for the synthesis of compounds 4a-4p
A mixture of 4-chloro-3-nitrobenzoic acid (25 mmol) and ethylaminesolution (0.1 mol) was stirred at 70 °C for 5 h. cooled toroom temperature, the resulting solution was poured into waterand acidized to pH 4-5 with AcOH. Filtering and drying, we obtainedyellow solid 4-substituted-3-nitrobenzoic acid. Yield 99%. |
95% |
In water at 80℃; |
synthesis of compound 6
The mixture of 4-chloro-3-nitrobenzoic acid (100 mmol)and a solution of ethylamine in water (60 %, 86 mL,800 mmol) was refluxed at 80 °C for 6 h. The mixture wasadjusted to pH 4-5 with acetic acid under ice-water bathto get the precipitation of yellow solid. Then compound 6(95 %) was obtained by filtering |
90% |
With acetic acid at 80℃; for 6h; |
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70% |
In water at 80℃; |
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at 75℃; for 5h; |
General procedure for synthesis of 3-[(3-chloro-4-fluorophenyl)-(4-substituted-3-nitrobenzoyl)amino]propionic acid ethyl ester (6a-6g)
General procedure: A mixture of 4-chloro-3-nitrobenzoic acid 3 (50 mmol) and the corresponding amine solution (865 mmol) was stirred at 75 °C for 5 h. After cooling, the resulting solution was poured into water, acidified to pH 4-5 with concentrated HCl, and the solid formed was isolated by filtration and dried to obtain 4-substituted-3-nitrobenzoic acid (4a-4g). |
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With acetic acid at 80℃; for 5h; |
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Reference:
[1]Chen, Haifeng; Ren, Yujie
[Archiv der Pharmazie, 2015, vol. 348, # 6, p. 408 - 420]
[2]Ren, Weixin; Ren, Yujie; Wang, Shuai
[European Journal of Medicinal Chemistry, 2016, vol. 120, p. 148 - 159]
[3]Wang, Fei; Ren, Yu-Jie
[Journal of the Iranian Chemical Society, 2016, vol. 13, # 6, p. 1155 - 1166]
[4]Wang, Fei; Ren, Yu-Jie; Dong, Ming-Hui
[Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 12, p. 2739 - 2753]
[5]Li, Meilin; Ren, Yujie
[Archiv der Pharmazie, 2015, vol. 348, # 5, p. 353 - 365]
[6]Li, Chun Lei; Ren, Yu Jie
[Research on Chemical Intermediates, 2016, vol. 42, # 2, p. 735 - 752]
[7]Huang, Shanshan; Ren; Peng, Xiuxiu; Qian, Pingping; Meng, Lingwei
[European Journal of Pharmaceutical Sciences, 2019, vol. 137]
- 3
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[ 67-56-1 ]
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[ 2788-74-1 ]
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[ 396652-42-9 ]
Yield | Reaction Conditions | Operation in experiment |
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With sulfuric acid for 6h; Reflux; |
Synthesis of methyl 4-(methylamino)-3-nitrobenzoate (s2):
General procedure: Synthesis of methyl 4-(methylamino)-3-nitrobenzoate (s2):3.6 g (18 mmol) 4-methylamino-3-nitro-benzoic acid (s1) was dissolved in 35 mL methanol, 1 mL concentrated sulfuric acid was added. The mixture was heated and maintained at reuxing temperature of 70°C for 6 h, then cooled and poured into 100 mL water, neutralized with saturated solution of sodium bicarbonate, extracted with 100 mL ethyl acetate, washed with 50 mL water and dried with anhydrous sodium sulfate overnight. The filtrate was concentrated by vacuum distillation to obtain yellow solid of s2 3 g,yield 77%. MS calcd. for: C9H10N2O4: 210.06, GC/MS: 210. |
Reference:
[1]Chang, Kang; Chen, Jian-Qin; Shi, Yan-Xia; Sun, Mei-Jian; Li, Peng-Fei; Zhao, Zhen-Jiang; Zhu, Wei-Ping; Li, Hong-Lin; Xu, Yu-Fang; Li, Bao-Ju; Qian, Xu-Hong
[Chinese Chemical Letters, 2017, vol. 28, # 4, p. 919 - 926]
- 4
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[ 2788-74-1 ]
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[ 343942-49-4 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: sulfuric acid / 6 h / Reflux
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 °C |
|
Reference:
[1]Chang, Kang; Chen, Jian-Qin; Shi, Yan-Xia; Sun, Mei-Jian; Li, Peng-Fei; Zhao, Zhen-Jiang; Zhu, Wei-Ping; Li, Hong-Lin; Xu, Yu-Fang; Li, Bao-Ju; Qian, Xu-Hong
[Chinese Chemical Letters, 2017, vol. 28, # 4, p. 919 - 926]
- 5
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[ 2788-74-1 ]
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[ 1354407-23-0 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 6 steps
1: sulfuric acid / 6 h / Reflux
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 °C
3: acetic acid; sodium nitrite / acetic acid / 18 h / 20 °C
4: sodium hydroxide / water / 4 h / 40 °C
5: oxalyl dichloride / dichloromethane / 1 h / 20 °C
6: triethylamine / dichloromethane / 5 h / 20 °C |
|
Reference:
[1]Chang, Kang; Chen, Jian-Qin; Shi, Yan-Xia; Sun, Mei-Jian; Li, Peng-Fei; Zhao, Zhen-Jiang; Zhu, Wei-Ping; Li, Hong-Lin; Xu, Yu-Fang; Li, Bao-Ju; Qian, Xu-Hong
[Chinese Chemical Letters, 2017, vol. 28, # 4, p. 919 - 926]