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ChemicalBook CAS DataBase List Ethyl 4-aminophenylacetate
5438-70-0

Ethyl 4-aminophenylacetate synthesis

11synthesis methods
A solution of (4-nitro-phenyl)-acetic acid ethyl ester (Preparation 266, 3.4 g, 16.1 mmol) in methanol (100 mL) was degassed with argon for 15 min, treated with 10% palladium on charcoal (700 mg), and then stirred at room temperature under hydrogen (balloon pressure) for 16 hours. The reaction mixture was filtered through celite, washed with methanol (2 × 20 mL) and the filtrate Ethyl 4-aminophenylacetate was evaporated in vacuo. Yield: 96%, 2.8 g, oil. 1H NMR (400 MHz, CDCl3) δ: 1.23 (t, 3H), 3.47 (s, 2H), 3.60 (br s, 2H), 4.11 (q, 2 H), 6.63 (d, 2H), 7.05 (d, 2H).
Ethyl 4-aminophenylacetate synthesis
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Yield:5438-70-0 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol for 4 h;

Steps:

12 Ethyl 2-(4-aminophenyl)acetate (4j).
A solution of ethyl 2-(4-nitrophenyl)acetate (3j) (1.05 g, 3.40 mmol) inMeOH (25 mL) was hydrogenated over 10% Pd/C (catalytic amount) for 4h. The catalyst was filtered off and the resultingsolution was concentrated to afford ethyl 2-(4-aminophenyl)acetate (4j). 1H-NMR 200 MHz (CDCl3) δ: 1.29 (t, 3H, J=7.2Hz ), 3.72 (s, 2H), 4.13 (q, 2H, J=7.2 Hz), 6.51 (d, 2H, J= 7.2 Hz), 6.98 (d, 2H, J= 7.2 Hz). Quantitative yield

References:

Leadiant Biosciences SA;GIANNINI, Giuseppe;SIMONI, Daniele;OLIVA, Paola;MOR, Marco;RIVARA, Silvia EP3381898, 2018, A1 Location in patent:Paragraph 0200; 0272

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