Molbank 2005, M433

3-Nitropyridin-2-yl hydrazone of 5-Acetyl-3-phenyl-1,2,4-triazine

Mariusz Mojzych

Institute of Chemistry, University of Podlasie,

ul. 3 Maja 54, 08-110 Siedlce, Poland

Received: 11 May 2004 / Accepted: 27 May 2004 / Published: 1 October 2005

Keywords: hydrazone, pyridin-2-yl hydrazine, 5-acetyl-1,2,4-triazine.

In continuation of previous work on the polyfunctionally substituted 1H-pyrazolo[4,3-e][1,2,4]triazine [1,2] we have reported here preparation of 3-nitropyridin-2-yl hydrazone of 5-acetyl-3-phenyl-1,2,4-triazine 3 being valuable intermediate for the synthesis of nitro derivative of this ring system.

To a solution of 5-acetyl-3-phenyl-1,2,4-triazine 1(199 mg, 1mmol)[3] and 3-nitropyridin-2-ylhydrazine 2 (185 mg, 1.2 mmol) in ethanol (30 ml) 10% HCl (0.5 ml) was added. The resulting reaction mixture was heated at reflux for 5 min and then was stirred at room temperature for 30 min. After that time the solvent was concentrated in vacuo. The solid was collected by filtration, washed with water and recrystallized from DMSO/water (1:1) to give compound 3 in 82% yield.

Melting Point: 255^ºC.

¹H-NMR (200 MHz, d6-DMSO): δ= 2.53 (s, 3H); 7.21-7.27 (m, 1H); 7.62-7.67 (m, 3H); 8.44-8.54 (m, 3H); 8.65-8.68 (m, 1H); 9.56 (s, 1H); 11.36 (s, 1H).

IR (CHCl₃ film, cm^-1): 3316; 3069; 1598; 1530; 1500; 1366; 1264; 1199; 1053; 754; 697.

MS-EI (m/z, %): 335 (1) [M⁺]; 189 (30); 180 (9); 179 (100); 157 (6); 143 (8); 133 (5); 128 (7); 103 (7); 102 (4); 77 (5).

HR-MS: Calculated for C₁₆H₁₃N₇O₂: 335.11307. Found: 335.11339.

References:

1.Rykowski, A.; Mojzych, M.; Karczmarzyk, Z. Heterocycles, 2000, 53, 2175.

2.Mojzych, M.; Rykowski A. Polish J. Chem., 2003, 77, 1797.

3.Rykowski, A.; Lipińska, T. Synth. Comm., 1996, 26, 4409.

Sample Availability: Available from MDPI.