Abstract: The title compound, ethyl 3-{2-[(3-methyl-1H-indol-2-yl)carbonyl]hydrazinylidene} butanoate (3), was prepared via reaction of 3-methyl-1H-indole-2-carbohydrazide (1) and ethyl 3-oxo­butanoate (2) under reflux. The structure of the synthesized compound was assigned on the basis of elemental analysis, IR, 1H-NMR, mass spectral and X-ray data.




http://www.mdpi.com/1422-8599/2012/1/M749

Molbank 2012, 2012(1), M749; doi:10.3390/M749

Short Note

Ethyl 3-{2-[(3-Methyl-1H-indol-2-yl)carbonyl]­hydrazinylidene}­butanoate

Thoraya A. Farghaly and Sobhi M. Gomha * 

 E-Mail: s.m.gomha@hotmail.com.

Department of Chemistry, Faculty of Science, University of Cairo, Giza 12613, Egypt

* Author to whom correspondence should be addressed.

DR SOBHI M GOMHA - UNIVERSITY OF CAIRO

http://cu.edu.eg/ar/Home

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Synthesis of Ethyl 3-{2-[(3-Methyl-1H-indol-2-yl)carbonyl]hydrazinylidene}butanoate (3)

A mixture of the hydrazide 1 (1.89 g, 10 mmol) and ethyl 3-oxobutanoate 2 (10 mmol) in absolute

ethanol (20 mL) was heated at reflux temperature for 2 h. The reaction mixture was then cooled and

the formed precipitate was filtered off, washed with ethanol to afford the title compound 3. Yield:

84%; yellow microcrystals (from ethanol); mp: 238–240 °C.

 IR (KBr): v 1706, 1668 (2 C=O), 3409,3234 (2 NH) cm−1

1H NMR (DMSO-d6): δ 1.24 (t, J = 7.0 Hz, 3H, CH3), 2.03 (s, 3H, CH3), 2.53 (s,

3H, CH3), 3.43 (s, 2H, CH2), 4.23 (q, J = 7.0 Hz, 2H, CH2), 6.87–7.98 (m, 4H, ArH ), 10.38 (s, 1H,

D2O exchangeable, NH), 11.21 (s, 1H, D2O exchangeable, NH). 

MS m/z (%): 301 (M+, 42), 189 (100),155 (318), 117 (46), 77 (21).

Anal. Calcd for C16H19N3O3 (301.34): C, 63.77; H, 6.36; N, 13.94. Found C, 63.39; H, 6.46; N, 13.65.

References and Notes

1. Ismail, M.F.; Shmeiss, N.A.M.M.; El-Diwani, H.I.; Arbid, M.S. Synthesis and pharmacological

activity of some 2,3-diphenylindole derivative. Indian J. Chem. Sect. B 1997, 36B, 288–292.

2. von Angerer, E.; Knebel, N.; Kager, M.; Ganss, B.J. 1-(Aminoalkyl)-2-phenylindoles as novel

pure Estrogen Antagonists. J. Med. Chem. 1900, 33, 2635–2640. 

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