This compound(3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine)Category: isoquinoline was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.
The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preparation of 1,2,4,5-tetrazines from pyridine and methylenedioxybenzene》. Authors are Dallacker, F..The article about the compound:3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-aminecas:1671-88-1,SMILESS:NN1C(C2=NC=CC=C2)=NN=C1C3=NC=CC=C3).Category: isoquinoline. Through the article, more information about this compound (cas:1671-88-1) is conveyed.
Pyridine-2-carbonitrile, the 3- and 4-isomer, and 3,4-methylenedioxybenzonitrile were treated with N2H4.H2O (I) to give the corresponding 1,2-dihydro-1,2,4,5-tetrazine (II), which was oxidized with HNO3 to the 1,2,4,5-tetrazine (III), or the pyridine compounds were rearranged with HCl to a 3,5-disubstituted-4-amino-1,2,4-triazole (IV). A mixture of 46.8 g. pyridinecarbonitrile and 200 ml. of 80% I was heated on a steam-bath and a small amount of Raney Ni added. Heating was continued until a solid formed, and after 10 min., 500 ml. ice water was added and 3,6-dipyridyl derivative of II separated and some IV remained in the filtrate. Thus prepared were II (pyridine isomer, m.p., crystallization solvent, % yield, and color given): 2, 194.2°, iso-PrOH, 85.5, yellow; 3, 235.2°, pyridine, 46.2, orange; 4, 275.5°, HOAc-H2O, 72.4, orange. Similarly, 49 g. 3,4-methylenedioxybenzonitrile, 150 ml. 80% I, and 23 g. H2NNH2.HCl gave 3,6-bis(3,4-methylenedioxyphenyl) derivative of II, m. 242.5° (HOAc), 51.8% yield, yellow. A solution of 2 g. 3,6-disubstituted derivative of II in 100 ml. HOAc was treated during 10 min. with 10 ml. 5N HNO3 and with cooling or by adding 1 ml. HNO3 gave the salt of III which was crystallized from pyridine (V) to give the base. Thus prepared were III (3,6-substitution, m.p., crystallization solvent, % yield, and color given): 2-pyridyl, 224.5°, iso-PrOH, 81.5, red; 3-pyridyl, 198.2°, EtOH, 80.4, blue-red; 4-pyridyl, 256.8°, HCONMe2, 89.4, violet; 3,4-methylenedioxyphenyl, 270.5°, HCONMe2, 98.5, red; 2-thienyl, 226.5°, EtOH, 40.2, red. A mixture of 10 g. 3,6-dipyridyl derivative of II and 200 ml. N HCl was heated 12-15 min. and the clear solution made alk. with N NH3 to give a crude product. This was heated for 5-6 hrs. with 50 g. Raney Ni in 3 l. iso-PrOH, filtered hot, and IV crystallized from the filtrate. Thus prepared were the following IV (3,5-substitution, m.p. crystallization solvent, and % yield given): 2-pyridyl, 184.8°, iso-PrOH, 45.2; 3-pyridyl, 275.5°, iso-PrOH, 63.2; 4-pyridyl, 328.6° (decomposition), H2O, 58.4. To a solution of 8 g. 3,6-bis(3,4-methylenedioxyphenyl) derivative of II in 300 ml. boiling HOAc was added 100 ml. N HCl. After heating the mass 10 min., it was concentrated in vacuo and 3,5-bis(3,4-methylenedioxyphenyl)-1,2,4-oxadiazole separated, m. 242.8° (HCONMe2), in 15% yield. Concentration of the filtrate gave 1,2-bis(3,4-methylenedioxybenzoyl)hydrazine, m. 234.5° (HOAc-H2O), in 24% yield. Infrared data supported the structures given.
This compound(3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine)Category: isoquinoline was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.
Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem