Alternatived Products of [ 20948-67-8 ]
Product Details of [ 20948-67-8 ]
| CAS No. : | 20948-67-8 |
MDL No. : | MFCD02585494 |
| Formula : |
C9H8ClN3O
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Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
209.63
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Pubchem ID : | - |
| Synonyms : |
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Safety of [ 20948-67-8 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 20948-67-8 ]
* 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 [ 20948-67-8 ]
- 2
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[ 10517-21-2 ]
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[ 20948-67-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
|
5-Chloro-1H-indole-2-carboxylic acid (1.96 g) and 1-hydroxybenzotriazole monohydrate (HOBt·H2O) (1.58 g) were dissolved in N,N-dimethylformamide (DMF) (10 ml) and 1-(3-(dimethylamino)propyl)-3-ethylcarhodiimide hydrochloride (EDC) (2.58 g) was added. This solution was stirred at room temperature for 3 hr. This solution was cooled in an ice-bath and hydrazine hydrate (2.4 ml) was added. This solution was stirred at room temperature for 11 hr. Water (20ml) was added slowly to this reaction mixture. The precipitated solid was collected by filtration and dried in vacuo to give the title compound (2.24 g) (containing DMF (15%) as a residual solvent). This sample was boiled in tetrahydrofuran (THF), allowed to cool and filtered to give a purer sample.1H-NMR(δ, 300MHz,DMSO-d6). 4.52(2H,brs),7.05(1H,d,J=1.5Hz),7.16(1H,dd,J=8.7Hz,2.1Hz),7.42 (1H,d,J=8.7Hz),7.66(1H,d,J=1.9Hz),9.86(1H,brs),11.84(1H,s). |
- 3
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[ 20948-67-8 ]
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[ 103-01-5 ]
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5-chloro-1H-indole-2-carboxylic acid 2-(anilinoacetyl)hydrazide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 94% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; for 13h; |
4.2.a Example 4-2N-(2,4-dioxo-1-phenylimidazolidin-3-yl)-5-chloro-1H-indole-2-carboxamide;a) 5-chloro-1H-indole-2-carboxylic acid 2-(anilinoacetyl)hydrazide
To a suspension (5 ml) of 5-chloro-1H-indole-2-carboxylic acid hydrazide obtained in Example 1 a) (210 mg) and anilinoacetic acid (151 mg) in DMF were added 1-hydroxybenzotriazole (184 g) and EDC (230 mg). The mixture was stirred at room temperature for 13 hr and water was added to the reaction solution. This mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate, water and saturated brine and dried over sodium sulfate. This solution was filtered and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to give the title compound (321 mg, yield 94%). |
- 4
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[ 3663-80-7 ]
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[ 20948-67-8 ]
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2,3-dihydrobenzo[1,4]dioxine-2-carboxylic acid N'-(5-chloro-1H-indole-2-carbonyl)hydrazide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 16h; |
To a solution of 5-chloro-lH-indole-2-carboxylic acid hydrazide (Preparation 1, 0. 50g, 2. 39mmol) in DMF (5rnL) was added HOBt (0. 32g, 2. 39mmol), DIPEA (0.83mL, 4. 78mmol) and 2,3-dihydrobenzo [1, 4] dioxine-2-carboxylic acid (0.43g, 2.39mmol) followed by EDCI (0. 55g, 2. 87mmol). The reaction mixture was stirred at rt for 16h, poured into water (75mL) and extracted with ethyl acetate (2 x 150mL). The combined organic extracts were washed with HCl (IN, 50mL), NaOH (1N, 50mL) and saturated sodium chloride solution (75mL). The organic layer was dried (MgS04) and concentrated in vacuo to give the title compound. m/z (ES+) = 372 [M+ H] + ; RT = 3. 57min. |
- 5
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[ 87802-11-7 ]
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[ 20948-67-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 95% |
With hydrazine hydrate In ethanol for 5h; Reflux; |
|
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With hydrazine hydrate |
|
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With hydrazine hydrate In methanol for 3h; Reflux; |
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Reference：
[1]Jiang, Hai-Xia; Zhuang, Dao-Min; Huang, Ying; Cao, Xing-Xin; Yao, Jian-Hua; Li, Jing-Yun; Wang, Jian-Yong; Zhang, Chen; Jiang, Biao
[Organic and Biomolecular Chemistry, 2014, vol. 12, # 21, p. 3446 - 3458]
[2]Location in patent: body text
Narayana; Ashalatha; Vijaya Raj; Sarojini
[Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 12, p. 1794 - 1805]
[3]Kilic-Kurt, Zühal; Acar, Cemre; Ergul, Mustafa; Bakar-Ates, Filiz; Altuntas, Tunca G.
[Archiv der Pharmazie, 2020, vol. 353, # 8]
- 6
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[ 20948-67-8 ]
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[ 84194-30-9 ]
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(E)-5-chloro-N’-(2-chloro-5-fluorobenzylidene)-1H-indole-2-carbohydrazide
[ No CAS ]
- 7
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[ 22062-53-9 ]
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[ 20948-67-8 ]
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(E)-5-chloro-N’-(5-fluoro-2-methylbenzylidene)-1H-indole-2-carbohydrazide
[ No CAS ]
- 8
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[ 20948-67-8 ]
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[ 177756-62-6 ]
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(E)-5-chloro-N’-(5-fluoro-4-methylbenzylidene)-1H-indole-2-carbohydrazide
[ No CAS ]
- 9
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[ 5779-93-1 ]
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[ 20948-67-8 ]
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(E)-5-chloro-N’-(2,3-dimethylbenzylidene)-1H-indole-2-carbohydrazide
[ No CAS ]
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