ETHYL 3-(4-AMINOPHENYL)PROPANOATE synthesis

15synthesis methods

Product Name:ETHYL 3-(4-AMINOPHENYL)PROPANOATE
CAS Number:7116-44-1
Molecular formula:C11H15NO2
Molecular Weight:193.24

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Yield:7116-44-1 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethanol at 0 - 20; for 16 h;

Steps:

4.1.3. General method C for the synthesis of ethyl 3-(4-aminophenyl)propanoate (12)

In a solution of ethyl 4-aminocinnamate (9, 0.382 g, 2 mmol, 1 eq.) in ethanol (30 mL), 0.240 g of 10% palladium on charcoal (10% Pd/C)was added at 0 C. Then, the reaction was kept under constant stirring atroom temperature under H2 atmosphere for 16 h. The product wasfiltered through a small pad of Celite, and concentrated to aford theproduct as a yellow liquid (0.386 g, quant.). 1H NMR (300 MHz, DMSOd6)δ 10.19 (s, 2H), 7.31 (d, J = 8.6 Hz, 2H), 7.27 (d, J = 8.6 Hz, 2H),4.04 (q, J = 7.1 Hz, 2H), 2.86 (t, J = 7.4 Hz, 2H), 2.62 (t, J = 7.4 Hz, 2H),1.15 (t, J = 7.1 Hz, 3H). 13C NMR (75 MHz, DMSO- d6) δ 172.0, 139.6,130.9, 129.3 (2C), 122.6 (2C), 59.8, 34.9, 29.7, 14.0.

References:

Tavares, Maurício Temotheo;de Almeida, Larissa Costa;Kronenberger, Thales;Monteiro Ferreira, Glaucio;Fujii de Divitiis, Thainá;Franco Zannini Junqueira Toledo, M?nica;Mariko Aymoto Hassimotto, Neuza;Agostinho Machado-Neto, Jo?o;Veras Costa-Lotufo, Letícia;Parise-Filho, Roberto [Bioorganic and Medicinal Chemistry,2021,vol. 35]