2-[5-chloro(bromo)-3-hydrazono-2-oxo-2,3-dihydro-1H-indolin-1-yl]acetohydrazide
by
Bouhfid Rachid
1,
Nicolas Joly
2,
Vincent Lequart
2,
Patrick Martin
2,
Mohammad Massoui
1 and
El Mokhtar Essassi
1,* 
1
Laboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie Université Mohammed V-Agdal, BP: 1014 Avenue Ibn Batouta, Rabat, Morocco
2
Blood-Brain Barrier Laboratory (EA 2465), IUT of Béthune, University of Artois, BP 819, 62408 Béthune, France
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(2), M537; https://doi.org/10.3390/M537
Submission received: 9 November 2006
/
Accepted: 4 December 2006
/
Published: 31 May 2007
Isatin derivatives exhibit significant biological, medicinal and pharmacological activities, [1,2] such as antituberculous, antihypoxing agent, anticonvulsant, antihyperglycemic; active against salmonella, typhi and against vibrio cholerae. Besides, they are used in treating and preventing pestvirus. [3] We describe in this work, the synthesis of new indoline derivatives.
To a solution of 1a-b (3.7 mmol) in 10 mL of ethanol, was added hydrazine hydrate (7.4 mmol). The mixture was refluxed for 6 h. After cooling the precipate was filtered and recrystallised from ethanol to afford product 2a-b.
2-[5-chloro-3-hydrazono-2-oxo-2,3-dihydro-1H-indolin-1-yl]acetohydrazide 2a: Yield: (74%). Melting Point: > 250°C. MS (IE): M+(m/z) = 267 (76%)/ 269 (25%); 180 (100%). υ (cm-1): 3310, 3285, 3113, 3091, 1675, 1654, 1598, 1532. 1H NMR (300 MHz, CDCl3): 3.52 (s, 2H, NH2), 4.12 (s, 2H, NH2); 4.61 (s, 2H, NCH2); 7.00-7.40 (m, 3H, HAr); 9.27 (s, 1H, NH). 13C NMR (300 MHz, CDCl3): 41.2 (NCH2); 111.2, 117.6, 126.9 (CHAr); 117.8, 124.6, 138.4 (Cq); 159.1 (C=Oamide); 161.4 (C=Nimine); 165.3 (C=Ohydrazide). Elemental analysis: Calculated for C10H10ClN5O2: C, 44.87%; H, 3.77%; N, 26.16%; Found: C, 44.62%; H, 3.88%; N, 25.96%.
2-[5-bromo-3-hydrazono-2-oxo-2,3-dihydro-1H-indolin-1-yl]acetohydrazide 2b: Yield: (70%). Melting Point: > 250°C. MS(IE): M+(m/z) = 311 (39%)/ 313 (37%); 224 (100%). υ (cm-1): 3320, 3279, 3162, 3089, 1687, 1656, 1599, 1533. 1H NMR (300 MHz, CDCl3): 3.34 (s, 2H, NH2), 4.06 (s, 2H, NH2); 4.57 (s, 2H, NCH2); 6.91-7.51 (m, 3H, HAr); 9.32 (s, 1H, NH). 13C NMR (300 MHz, CDCl3): 40.6 (NCH2); 111.4, 120.4, 129.6 (CHAr); 115.0, 124.6, 138.7 (Cq); 159.0 (C=Oamide); 161.2 (C=Nimine); 167.2 (C=Ohydrazide). Elemental analysis: Calculated for C10H10BrN5O2: C, 38.48%; H, 3.23%; N, 22.44%; Found: C, 38.31%; H, 3.35%; N, 22.56%.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6References
- Pandeya, S.N.; Sriram, D. Acta Pharm. Turc. 1998, 40, 33.
- Sarangapani, M.; Narayan, A.R.; Jayamma, Y.; Reddy, V.M. Indian Drugs 1998, 35, 336.
- Pevear, C.D.; Nitz, J.T.; Seipel, M. PCT Int. Appl. WO98 36,752; (Cl.A61K3 1/555)27 Aug 1998, US Appl. 12 Feb. 1997, 803, 675,
- Joshi, K.C.; Jam, R.; Chand, P.; Garg, S. J. Indian Chem. Soc. 1983, LX, 760.
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MDPI and ACS Style
Rachid, B.; Joly, N.; Lequart, V.; Martin, P.; Massoui, M.; Essassi, E.M. 2-[5-chloro(bromo)-3-hydrazono-2-oxo-2,3-dihydro-1H-indolin-1-yl]acetohydrazide. Molbank 2007, 2007, M537. https://doi.org/10.3390/M537
AMA Style
Rachid B, Joly N, Lequart V, Martin P, Massoui M, Essassi EM. 2-[5-chloro(bromo)-3-hydrazono-2-oxo-2,3-dihydro-1H-indolin-1-yl]acetohydrazide. Molbank. 2007; 2007(2):M537. https://doi.org/10.3390/M537
Chicago/Turabian StyleRachid, Bouhfid, Nicolas Joly, Vincent Lequart, Patrick Martin, Mohammad Massoui, and El Mokhtar Essassi. 2007. "2-[5-chloro(bromo)-3-hydrazono-2-oxo-2,3-dihydro-1H-indolin-1-yl]acetohydrazide" Molbank 2007, no. 2: M537. https://doi.org/10.3390/M537
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