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| | Ethyl 4,6-dichloro-1H-indole-2-carboxylate Basic information |
| Product Name: | Ethyl 4,6-dichloro-1H-indole-2-carboxylate | | Synonyms: | 4,6-DICHLOROINDOLE-2-CARBOXYLIC ACID ETHYL ESTER;4,6-DICHLORO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER;ETHYL 4,6-DICHLORO-1H-INDOLE-2-CARBOXYLATE;ETHYL 4,6-DICHLOROINDOLE-2-CARBOXYLATE;ETHYL,4,6-DICLOROINDOLE-2-CARBOXYLATE;1H-Indole-2-carboxylic acid, 4,6-dichloro-, ethyl ester;Ethyl 4,6-dichloro-1H-indole-2-carboxylate 97%;ethyl pyruvate-3,5-di-chlorophenylhydrazone | | CAS: | 53995-82-7 | | MF: | C11H9Cl2NO2 | | MW: | 258.1 | | EINECS: | | | Product Categories: | Indoles and derivatives;Heterocyclic Compounds | | Mol File: | 53995-82-7.mol |  |
| | Ethyl 4,6-dichloro-1H-indole-2-carboxylate Chemical Properties |
| Melting point | 171-172 | | Boiling point | 405.0±40.0 °C(Predicted) | | density | 1.432±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C, protect from light | | pka | 13.21±0.30(Predicted) | | Appearance | White to off-white Solid | | CAS DataBase Reference | 53995-82-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Hazard Note | Irritant | | HS Code | 2933998090 |
| | Ethyl 4,6-dichloro-1H-indole-2-carboxylate Usage And Synthesis |
| Uses | Ethyl 4,6-dichloro-1H-indole-2-carboxylate is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.
| | Synthesis | Step 3: Preparation of the intermediate ethyl 4,6-dichloro-1H-indole-2-carboxylate (I-ic)
Ethyl 2-[2-(3,5-dichlorophenyl)hydrazin-1-ylidene]propanoate (26 g, 94.50 mmol in two batches) was reacted with polyphosphoric acid (260 g, each batch) at 110 °C with stirring for 3 hours. Upon completion of the reaction, the reaction mixture was slowly poured into crushed ice, stirred thoroughly and the precipitate was collected by filtration. The resulting solid was alkalized with saturated aqueous NaHCO3 (adjusted pH to 10) and subsequently extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography using a hexane solution of 30% ethyl acetate as eluent to afford ethyl 4,6-dichloro-1H-indole-2-carboxylate (I-ic) 36 g in 73.8% yield as an off-white solid.
1H NMR (400 MHz, DMSO-d6): δ 12.46 (s, 1H), 7.46 (s, 1H), 7.30 (s, 1H), 7.12 (s, 1H), 4.36 (q, J = 7.2 Hz, 2H), 1.35 (t, J = 7.2 Hz, 3H).
ESI MS: m/z 255.8 (M-H). | | References | [1] Patent: WO2006/109633, 2006, A1. Location in patent: Page/Page column 182-183
[2] Organic Process Research and Development, 2000, vol. 4, # 6, p. 477 - 487
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 326 - 330
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2011, vol. 54, # 10, p. 645 - 656
[5] ACS Infectious Diseases, 2017, vol. 3, # 3, p. 225 - 236 |
| | Ethyl 4,6-dichloro-1H-indole-2-carboxylate Preparation Products And Raw materials |
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