| Identification | Back Directory | [Name]
ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE | [CAS]
174775-48-5 | [Synonyms]
Vilazodone INT 5
ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLAT
ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE
5-Amino-2-(ethoxycarbonyl)-1-benzofura
5-Amino-2-(ethoxycarbonyl)-1-benzofuran
Ethyl 5-aminobenzo[b]furan-2-carboxylate
ethyle5-aminobenzo[b]furan-2-carboxylate
Ethyl 5-amino-1-benzofuran-2-carboxylate (en)
ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE USP/EP/BP
2-Benzofurancarboxylicacid, 5-aMino-, ethyl ester
2-Benzofurancarboxylicacid,5-amino-,ethylester(9CI)
5-Amino-2-(ethoxycarbonyl)-1-benzofuran, Ethyl 5-amino-1-benzofuran-2-carboxylate | [EINECS(EC#)]
1806241-263-5 | [Molecular Formula]
C11H11NO3 | [MDL Number]
MFCD08275091 | [MOL File]
174775-48-5.mol | [Molecular Weight]
205.21 |
| Chemical Properties | Back Directory | [Melting point ]
54-56°C | [Boiling point ]
348.1±22.0 °C(Predicted) | [density ]
1.258±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
soluble in Chloroform, DMSO | [form ]
Powder | [pka]
3.32±0.10(Predicted) | [color ]
Beige |
| Hazard Information | Back Directory | [Chemical Properties]
Brown Solid | [Uses]
Ethyl 5-aminobenzofuran-2-carboxylate is used as an synthetic intermediate in the preparation of indolebutylpiperazines, a class of dual 5-HT1A receptor agonists and serotonin reuptake inhibitors. Ethyl 5-amino-1-benzofuran-2-carboxylate was also used as a potential radiolabelled analog for melanoma imaging and targeted radiotherapy.
| [Synthesis]
General procedure for the synthesis of ethyl 5-aminobenzofuran-2-carboxylate from ethyl 5-nitrobenzofuran-2-carboxylate: 20.0 g of ethyl 5-nitrobenzofuran-2-carboxylate was placed in a reaction flask and 300 mL of ethanol was added as a solvent. Subsequently, 2 g of 5% Pd/C catalyst was added. The reaction system was replaced twice with hydrogen to ensure that the reaction environment was a hydrogen atmosphere. The hydrogenation reaction was carried out for 3 hours by adjusting the hydrogen pressure to 0.3-0.5 MPa and controlling the reaction temperature in the range of 10-30°C. The reaction was carried out by filtration. Upon completion of the reaction, the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure and dried to give 17.1 g of ethyl 5-aminobenzofuran-2-carboxylate in 98% yield. | [References]
[1] Patent: WO2013/153492, 2013, A2. Location in patent: Page/Page column 23
[2] Patent: US2015/87835, 2015, A1. Location in patent: Paragraph 0125
[3] ChemCatChem, 2014, vol. 6, # 11, p. 3153 - 3159
[4] Patent: CN107674052, 2018, A. Location in patent: Paragraph 0035-0037
[5] Patent: CN107540646, 2018, A. Location in patent: Paragraph 0041; 0042; 0043 |
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