ETHYL 2-AMINO-5-CHLORO-1H-INDOLE-3-CARBOXYLATE synthesis
- Product Name:ETHYL 2-AMINO-5-CHLORO-1H-INDOLE-3-CARBOXYLATE
- CAS Number:365547-91-7
- Molecular formula:C11H11ClN2O2
- Molecular Weight:238.67
62567-91-3
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Yield:365547-91-7 46.1 g
Reaction Conditions:
with acetic acid;zinc at 55; for 2.5 h;
Steps:
3.3. Ethyl 2-amino-5-chloro-1H-indole-3-carboxylate (7) : Compound 7 was prepared according to modified literature conditions.13 Crude 5 (60 g, 221 mmol) was dissolved in glacial acetic acid (600 ml) and zinc dust (40 g) was added after parts during 45 min. The mixture was stirred for 2 h without external heating (reaction is exothermic, temperature in the flask reached 55 C during reaction) and filtered through a pad of cellite. The pad was washed with acetic acid (400 ml) and solution was evaporated. The residue was then washed well with water and dried under reduced pressure. Compound 7 (46.1 g, 88%) was obtained as brown powder and further purified by column chromatography (hexane/chloroform,0-60% chloroform); mp: 190-193 C. 1H NMR is in agreement with literature.20 Crude material was used directly for the next step.
References:
Tichy, Michal;Pohl, Radek;Hocek, Michal;Xu, Hao Ying;Chen, Yen-Liang;Yokokawa, Fumiaki;Shi, Pei-Yong [Bioorganic and medicinal chemistry,2012,vol. 20,# 20,p. 6123 - 6133,11]
63069-48-7
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