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ChemicalBook CAS DataBase List 1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE

1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE synthesis

7synthesis methods
-

Yield:1484-04-4 70.47%

Reaction Conditions:

with aluminum (III) chloride in dichloromethane at 20; for 4 h;

Steps:

2.3.1. Synthesis of compound 2
N-Ethylcarbazole (0.05 mol, 9.75 g) was dissolved in CH2Cl2(150 mL), and then anhydrous AlCl3 (0.06 mol, 8.00 g) was quicklyadded with stirring to the reaction systemwith an ice bath. Then, aceticanhydride (0.075 mol, 5.30 ml) dissolved in CH2Cl2 (5 ml) was addeddropwise and the solution was stirred at room temperature for 4 h.The reaction solution was poured over ice-water and extracted withCH2Cl2. The organic phase was adjusted to pH 7 with sodium carbonatesolution, and dried with anhydrous magnesium sulfate. The precipitate was filtered and the solvent was evaporated in vacuo to give a greensolid. In the end, the pure product was given by recrystallization fromethanol (8.36 g, 70.47%). 1H NMR (600 MHz, DMSO-d6): δ 8.87 (s, 1H),8.31 (d, J = 7.7 Hz, 1H), 8.09 (d, J = 8.6 Hz, 1H), 7.69-7.67 (m, 2H),7.52 (t, J = 7.7 Hz, 1H), 7.29 (t, J = 7.4 Hz, 1H), 4.49 (q, J = 7.1 Hz,2H), 2.68 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H). 13C NMR (151 MHz,DMSO-d6): δ 197.45, 142.66, 140.76, 128.87, 126.94, 126.50, 123.04,122.51, 122.36, 121.28, 120.25, 110.16, 109.33, 37.72, 27.16, 14.17.(Fig. S1 and Fig. S2).

References:

Chao, Jianbin;Xu, Miao;Zhang, Yongbin;Huo, Fangjun;Liu, Yaoming;Wang, Xiaolu;Yin, Caixia [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2019,vol. 214,p. 227 - 232]

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