ETHYL 3-AMINOCROTONATE synthesis
- Product Name:ETHYL 3-AMINOCROTONATE
- CAS Number:626-34-6
- Molecular formula:C6H11NO2
- Molecular Weight:129.16
141-97-9
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Yield:626-34-6 100%
Reaction Conditions:
with ammonium carbamate in methanol at 20; for 1.5 h;
Steps:
To a solution of ethyl acetoacetate 9 (19.4 mL, 154 mmol)in methanol (160 mL) ammonium carbamate 8 (11.7 g, 154 mmol) was added in one portion.The resulting suspension was stirred at room temperature for 1.5 h. During that time all solidmaterial dissolved to give a clear yellow solution. The reaction mixture was concentrated todryness yielding title compound 7 (19.8 g, 153 mmol, quant.) as yellow liquid. 1H-NMR (400MHz, CDCl3), δ (ppm): 7.62 (b, 2H, NH2), 4.30 (s, 1H, CH), 3.90 (q, JHH 7.1 Hz, 2H, CH2CH3),1.71 (s, 3H, CH3), 1.06 (t, JHH 7.1 Hz, 3H, CH2CH3); 13C{1H}-NMR (101 MHz, CDCl3), δ(ppm): 170.5 (s, C=O), 160.6 (s, C-NH2), 83.7 (s, CH), 58.6 (s, CH2CH3), 22.2 (s, CH3), 14.8(s,CH2 CH3); TLC: Rf 0.36 (SiO2, cyclohexane/EtOAc 1:1)
References:
Auth, Johanna;Mauleon, Pablo;Pfaltz, Andreas [ARKIVOC,2014,vol. 2014,# 3,p. 154 - 169]
