5-chloro-1-methyl-1H-indole-2,3-dione

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5-chloro-1-methyl-1H-indole-2,3-dione Basic information
Product Name:5-chloro-1-methyl-1H-indole-2,3-dione
Synonyms:5-Chloro-1-methylisatin;5-chloro-1-methyl-1H-indole-2,3-dione;1-Methyl-5-chloroindoline-2,3-dione;Einecs 262-231-5;5-chloro-1-methyl-1H-indole-2,3-dione(SALTDATA: FREE);1H-Indole-2,3-dione, 5-chloro-1-methyl-;5-Chloro-1-methyl-2,3-indolinedione;5-Chloro-1-methylindole-2,3-dione
CAS:60434-13-1
MF:C9H6ClNO2
MW:195.6
EINECS:262-231-5
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Mol File:60434-13-1.mol
5-chloro-1-methyl-1H-indole-2,3-dione Structure
5-chloro-1-methyl-1H-indole-2,3-dione Chemical Properties
Melting point 175.0 to 179.0 °C
storage temp. Sealed in dry,Room Temperature
form powder to crystal
color Orange to Red
λmax426nm(EtOH)(lit.)
Safety Information
HS Code 2933998090
MSDS Information
5-chloro-1-methyl-1H-indole-2,3-dione Usage And Synthesis
Synthesis Reference(s)Journal of Medicinal Chemistry, 39, p. 5072, 1996 DOI: 10.1021/jm960603e
Synthesis
Acetamide, N-(4-chlorophenyl)-N-methyl-2-oxo-

872305-97-0

5-chloro-1-methyl-1H-indole-2,3-dione

60434-13-1

GENERAL METHODS: A mixture of N-methyl-2-oxo-N-phenylacetamide (0.4 mmol) and ferric chloride (10 mol%) was dissolved in 2 mL of dimethylsulfoxide (DMSO), and the reaction was stirred for 1.5 h at 100 °C under air atmosphere. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. Purification of the crude product by rapid column chromatography on silica gel (petroleum ether/ethyl acetate = 10:1) afforded 1-methyldihydroindole-2,3-dione as a red solid (60 mg, 93% yield).

References[1] RSC Advances, 2015, vol. 5, # 125, p. 103280 - 103283
[2] Tetrahedron Letters, 2016, vol. 57, # 1, p. 39 - 42
[3] Synlett, 2016, vol. 27, # 8, p. 1292 - 1296
[4] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8900 - 8902
[5] Chemistry - A European Journal, 2007, vol. 13, # 4, p. 1032 - 1046
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