5-Amino-thiophene-2-carboxylic acid methyl ester synthesis

6synthesis methods

Product Name:5-Amino-thiophene-2-carboxylic acid methyl ester
CAS Number:14597-58-1
Molecular formula:C6H7NO2S
Molecular Weight:157.19

5-NITROTHIOPHENE-2-CARBOXYLICMETHYLESTER

5832-01-9

5-Amino-thiophene-2-carboxylic acid methyl ester

14597-58-1

General procedure for the synthesis of methyl 5-amino-2-thiophenecarboxylate from methyl 5-nitro-2-thiophenecarboxylate: Methyl 5-nitro-2-thiophenecarboxylate (11.55 mmol) was dissolved in ethanol (20 mL), and 10% palladium carbon catalyst (1 g) was added. The reaction mixture was hydrogenated overnight with stirring under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was subsequently concentrated to afford the target product methyl 5-amino-2-thiophenecarboxylate (1.67 g, 92% yield). The product was detected by LCMS (ESI) and showed a molecular ion peak of 157 [M+H]+.

5832-01-9 Synthesis

5832-01-9
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14597-58-1
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Yield: 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethyl acetate at 20; for 2 h;

Steps:

Step 1: Methyl 5-aminothiophene-2-carboxylate
Into a 30-mL round-bottom flask purged and maintained with 1 atmosphere of hydrogen gas, was placed methyl 5-nitrothiophene-2-carboxylate (500 mg, 2.67 mmol), 10% Pd/C (500 mg, 0.47 mmol) in EA (10 mL). The resulting solution was stirred 2.0 h at room temperature. The reaction progress was monitored by LCMS. The mixture was filtered through a CELITE pad. The resulting mixture was concentrated under vacuum to yield methyl 5-aminothiophene-2-carboxylate as a white solid (420 mg, 100% yield). Mass spectrum (ESI, m/z): Calculated for C₆H₇NO₂S, 157.0, Measured: 158.3 [M+H]⁺.

References:

Zhang, Xuqing;Zhu, Bin;Sun, Weimei;Wang, Mina;Albarazanji, Kamal;Ghosh, Brahma;Cummings, Maxwell;Lenhard, James;Leonard, James;Macielag, Mark;Lanter, James [Bioorganic and Medicinal Chemistry Letters,2021,vol. 40,art. no. 127939] Location in patent:supporting information

527-72-0 Synthesis