Molbank 2007, M535

http://www.mdpi.org/molbank/

 

1-benzyl-3-(2-(pyridin-2-yl)hydrazono)indolin-2-one

 

Bouhfid Rachid 1, Nicolas Joly 2, Vincent Lequart 2, Patrick Martin 2, Mohamed  Massoui 1 and El Mokhtar Essassi 1,*

  

1 Laboratoire de Chimie Organique H¨¦t¨¦rocyclique, Pôle de comp¨¦tences Pharmacochimie Universit¨¦ Mohammed V-Agdal, BP: 1014 Avenue Ibn Batouta, Rabat, Morroco

2 Blood-Brain Barrier Laboratory (EA 2465), IUT of B¨¦thune, University of Artois, BP 819, F-62408 B¨¦thune

*Author to whom correspondence should be addressed.. E-mail: [email protected]

 

Received: 9 November 2006 / Accepted: 4 December 2006 / Published: 31 May 2007

 

Keywords: isatin, hydrazinopyridine, indoline.

 

Indole derivatives fall into an important class of organic compounds. These compounds are found in various natural products as fundamental nuclei and are well recognized for their wide spectrum of pharmacological and biochemical behavior. They have received the attention of biochemists because of their therapeutic and biochemical activities [1-3].
We report in this work the synthesis of new indoline derivatives.

 

To a solution of 1 (1 g, 4.2 mmol) in 10 mL of ethanol, was added 2-hydrazinopyridine hydrochloride 2 (0.62 g, 4.2 mmol). The mixture was refluxed for 10 h. The precipitate was filtered and washed with ethanol to give compound 3, which was recrystallized from methanol.

Yield:  (83%). 

Melting Point: 155 ¡ãC.

 

MS (EI): M( m/z) = 328.

 

1H NMR (300 MHz, CDCl3): 5.05 (s, 2H, NCH2); 6.55-8.30 (m, 3H, HAr); 12.91 (s, 1H, NH).

 

13C NMR (300 MHz, CDCl3): 43.3 (NCH2); 108.1, 109.5, 118.3, 119.4, 122.7, 127.3, 127.7, 128.8, 138.1, 148.2 (CHAr); 121.0, 128.7, 135.6, 141.0 (Cq); 155.3 (C=Nimine); 161.7 (C=Oamide).

 

Elemental analysis: Calculated for C20H16N4O: C, 73.15%; H, 4.91%; N, 17.06%; Found: C, 73.01%; H, 5.05%; N, 16.89%.

 

References:

 

1. Verma, M.; Pandeya, S.N.; Singh, K.N.; Stables, J.P. Acta Pharm. 2004, 54, 49.

2. Guengerich, F.P.; Sorrells, J.L.; Schmitt, S.; Krauser, J.A.; Aryal, P.; Meijer, L. J. Med. Chem. 2004, 47, 3236.

3. Pirrung, M.C.; Pansare, S.V.; Sarma, K.D.; Keith, K.A.; Kern, E.R. J. Med. Chem. 2005, 48, 3045.

 

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