3-AMINOCINNAMIC ACID ETHYL ESTER synthesis

9synthesis methods

Product Name:3-AMINOCINNAMIC ACID ETHYL ESTER
CAS Number:125872-97-1
Molecular formula:C11H13NO2
Molecular Weight:191.23

621-19-2 Synthesis

621-19-2
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125872-97-1
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Yield:125872-97-1 100%

Reaction Conditions:

Stage #1: (E)-ethyl 3-(3-nitrophenyl)acrylatewith ethanol;water;tin(ll) chloride at 60; for 2 h;
Stage #2: with sodium hydrogencarbonate;Rochelle's salt in water;

Steps:

7.p.i

(p) 3- (3- [ (5-Phenyl-furan-2-carbonyl)-amino)-phenyl)-acrylic acid (61); (i) 3- (3-Amino-phenyl)-acrylic acid ethyl ester (60); 3- (3-Nitro-phenyl)-acrylic acid ethyl ester (500 mg, 2.3 mmol) was reduced using Method J to give the title compound. Yield: 430 mg, 100% ; LC-MS tr0. 92 min; MS (ES+) m/z 192 (M+H); J); The nitro derivative was dissolved in EtOH (5 vol) and SnCl2. 2H20 (50 eq) was added as a solid. The resulting solution was then stirred at 60°C for 2 h. After cooling to room temperature, a pre-mixed solution of saturated Rochelle's salt (10 vol) and saturated NaHC03 (10 vol) was added to the reaction mixture and the aqueous layer was extracted with EtOAc (3 x 20 vol). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to afford the product.

References:

WO2005/80367,2005,A1 Location in patent:Page/Page column 68; 115

59114-88-4 Synthesis