ChemicalBook CAS DataBase List 1-(1-METHYL-1H-INDOL-3-YL)-1-ETHANONE

1-(1-METHYL-1H-INDOL-3-YL)-1-ETHANONE synthesis

11synthesis methods

Product Name:1-(1-METHYL-1H-INDOL-3-YL)-1-ETHANONE
CAS Number:19012-02-3
Molecular formula:C11H11NO
Molecular Weight:173.21

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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75-36-5 Synthesis

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19012-02-3
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Yield: 56%

Reaction Conditions:

with sodium iodide in 1,2-dichloro-ethane for 16 h;Reflux;

Steps:

1-(1-Methyl-1H-indol-3-yl)ethan-1-one (12).
NaI (450 mg, 3 mmol) and AcCl (236 mg, 3 mmol) was successively added to a solution of 10b (213 mg,1 mmol) in DCE (30 mL) at room temperature and reflux for 16 h. The mixture was concentrated invaccuo, and the residue was diluted with H2O (30 mL). The mixture was extracted with AcOEt (3 x 50mL), washed with brine, and dried over MgSO4. The solvent was removed, and the residue was purifiedby silica gel column chromatography and purified by silica gel column chromatography withhexane/AcOEt (5/1) to give 12 (97 mg, 56%) as yellow oil.97 mg, 56%. Yellow oil. IR (CHCl3): 1684, 1670 cm-1. 1H-NMR (CDCl3) δ: 2.57 (s, 3H), 3.86 (s, 3H),7.32-7.35 (m, 3H), 7.77 (s, 1H), 8.33-8.35 (m, 1H). 13C-NMR (CDCl3) δ: 27.1, 33.8, 109.9, 116.7, 122.7,123.1, 123.7, 126.2, 136.9, 137.7, 194.7. HR-ESI-MS m/z: Calcd for C11H12NO [(M+H)+]: 174.0919.Found 174.0923.

References:

Abe, Takumi [Heterocycles,2018,vol. 96,# 3,p. 490 - 500]