2-(5,7-DICHLORO-1H-INDOL-3-YL)-ETHYLAMINE HYDROCHLORIDE synthesis
- Product Name:2-(5,7-DICHLORO-1H-INDOL-3-YL)-ETHYLAMINE HYDROCHLORIDE
- CAS Number:94850-28-9
- Molecular formula:C10H11Cl3N2
- Molecular Weight:265.56
6346-09-4
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5446-18-4
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94850-28-9
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Yield:94850-28-9 84%
Reaction Conditions:
with sulfuric acid in water at 100; for 2 h;
Steps:
Step-1: Synthesis of 2-(5, 7-dichloro-1H-indol-3-yl)ethan-1-amine
2,4-Dichlorophenyl)hydrazine hydrochloride (5.0 g, 23.5 mmol) was suspended in 4% aqueous sulphuric acid (150 mL) and 4-amino butyraldehyde diethyl acetal (4.53 g, 28.mmol, 1.2 eq) was added to the suspension. The reaction mixture was heated to 100 °C and monitored by LCMS. The reaction was complete after 2 h. The reaction mixture was then cooled to RT and the pH was adjusted to 10-12 with aqueous NaOH (1N, 90 mL). The aqueous layer was extracted with CH2Cl2 (2 × 250 mL). The combined organic layers were dried over anhydrous Na2SO4 filtered and concentrated to obtain 4 g of 2-(5,7-dichloro-1H-indol-3-yl)ethan-1-amine as a semi-solid. To this was added ethanolic HCl (150 mL) until the pH of the solution was 2-3. The solution was then concentrated under vacuum to remove to obtain 2-(5, 7-dichloro-1H-indol-3-yl) ethan-1-amine hydrochloride (4.5 g, 84%).LCMS: 228.02 [M+1]+.
References:
Rai, Roopa;Banerjee, Monali;Wong, Darren H.;McCullagh, Emma;Gupta, Ashu;Tripathi, Shailendra;Riquelme, Eduardo;Jangir, Ramnivas;Yadav, Shyamraj;Raja, Mohd.;Melkani, Pankaj;Dixit, Vikas;Patil, Umesh;Shrivastava, Ritesh;Middya, Sandip;Olivares, Felipe;Guerrero, Javier;Surya, Arjun;Pham, Son M.;Bernales, Sebastián;Protter, Andrew A.;Hung, David T.;Chakravarty, Sarvajit [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 20,p. 5103 - 5109]
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2664-85-9
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94850-28-9
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2701-26-0
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94850-28-9
11 suppliers
$43.00/1mg