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ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE

Product NameETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE
CAS174775-48-5
MFC11H11NO3
MW205.21
EINECS1806241-263-5
MOL File174775-48-5.mol

Chemical Properties

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

Safety Information

Hazard Codes	Xi
HazardClass	IRRITANT
HS Code	2932990090

Usage And Synthesis

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.

Uses

Ethyl 5-amino-1-benzofuran-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

69604-00-8

174775-48-5

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

ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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