3-Chloro-2-hydrazinylpyridine

In a reaction flask, 70 g of 2, 3-dichloropyridine and 250 ml of ethanol having a mass concentration of 95percent were added, 125ml of hydrazine hydrate with a mass concentration of 50percent was added dropwise under vigorous stirring, After completion of the dropwise addition, Heated to reflux 25h, Cooled to room temperature, A large number of white crystal precipitation, filtration, drying in 3-chloro-2-hydrazinopyridine148g of 2, 3-dichloropyridine and 3700g of N, N-dimethyl propanolamine in the reactor were mixed, Add 105g 80percent hydrazine hydrate, The atmosphere was replaced with nitrogen three times with nitrogen, Then warmed to 130 ° C, Insoluble reaction was refluxed for 10 hours, The reaction is over, Cooled to 25 crystallization, Then transferred to a centrifuge centrifuge, And washing the centrifuged solid with water, Centrifugal mother liquor into N, N- dimethyl propanolamine mother liquor tank for distillation, After centrifugation, the solid was sent to a double cone dryer (-0.09 MPa, 60 ° C.)In dry, The product 3-chloro-2-hydrazinopyridine.The purity of 3-chloro-2-hydrazinopyridine in step (b) was 99.7percentThe yield is 95percentLiquid chromatogram shown in Figure 2.To a 1 L three-necked flask was added 148.02 g (1.0 mol) of b-1 and 500 ml of 85percent hydrazine hydrate, Mechanical stirring under reflux 4h, After a period of reflow, the reaction solution becomes clear, TLC test reaction, the raw material reaction is complete, standing, the reaction solution to precipitate a large number of white crystals, the reaction solution into 800ml of water, magnetic stirring, the reaction precipitation more crystals, filter, filter cake were washed with 200ml water three times, The infrared lamp was dried to give a white needle-like crystal B-2 having a weight of 137 g and a yield of 94percent.Step A:Add 50percent hydrazine hydrate 20m L to 2, 3-dichloropyridine at room temperature(7.35g, 0.05mol) in 20mL ethanol solution, heated to reflux for 5h, Cool to room temperature and collect white acicular solid product by filtration3-chloro-2-mercaptopyridine 6.75g, yield 94.4percentA mixture of 2, 3-dichloropyridine (0.06 mol)80percent hydrazine hydrate (0.30 mol) andN-butanol 60 ml was added to a 100 ml three-necked flask and heated to a weak refluxing reaction overnight.After completion of the reaction, the solvent was distilled off to give 8.0 g of a white solid of (III) 3-chloro-2-hydrazinopyrid in a yield of 93percent.To a stirred solution of 4c (5.00 g, 33.8 mmol) in EtOH (25 mL) was added hydrazine monohydrate (6.77 g, 135 mmol), and the mixture was heated to reflux for 20 h. In 500 ml round-bottomed flask, followed by adding 50 g of 2, 3-dichloropyridine in 150 ml of ethanol, 127 g of 80percent hydrazine hydrate was heated at reflux for 26 hours with stirring, TLC monitored the reaction was completed, the reaction system was lowered to room temperature , the precipitated solid was filtered, the filter cake washed with water and dried to give white needle crystals, yield 90.13percent.A mixture of 50 mmol of 2, 3-pyridine V, 100 mmol of hydrazine hydrate, 50 ml of ethanol was added to a 100 ml three-necked round bottom flask, Was heated under reflux for 20 hours 80 ° C, The solvent was distilled off under reduced pressure, The resulting solid was recrystallized from ethanol to give acicular crystals3-chloro-2-hydrazinopyridine VI 6.5 g, Yield 90percent.50 mmol of 2, 3-pyridine are addedV, 100 mmol of hydrazine hydrate, 50 ml of ethanol was added to a 100 ml three-necked round bottom flask, heated to reflux for 20 hours at 80 degrees Celsius, The solvent was distilled off under reduced pressure, The resulting solid was recrystallized from ethanol to give acicular crystals3-Chloro-2-hydrazinopyridine VI 6.5 g, yield 90percent.A mixture of 2, 3-dichloropyridine (25.0 g), 80percent hydrazine hydrate (12.69 g) was stirred in refluxing EtOH (40 mL), the reaction proceeding was monitored by TLC. After complication of the reaction, the resulting mixture was cooled to room temperature to get white needle crystal (20.76 g), yield, 85.59percent, m.p. 163–164 °C.To a solution of 2, 3-dichloropyridine (50.0 g) in EtOH (40 mL), 25 g hydrazinehydrate (80percent) was added and refluxed for 24 h. The resulting mixture was cooled to room temperature, which was filtered and dried to get white needle crystal (41.5 g), yield: 85.6percent, m.p. 163–164°C.a. In a three-necked flask, 0.3 mol of 2, 3-dichloropyridine, 0.85 mol of hydrazine hydrate was added, and 350 mL of ethanol was added and the mixture was stirred at 70 ° C for 12 h.b. After the completion of the reaction to stop heating, cooling, white needle-like crystal precipitation, decompression filtration, washing the crystal, dry, that is, 3-chloro-2-hydrazinopyridine, the yield of 80percent, purity ≥ 98percent

This product is used as pesticide and pharmaceutical intermediate

Molecular Weight:143.57
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:143.0250249
Monoisotopic Mass:143.0250249
Topological Polar Surface Area:50.9
Heavy Atom Count:9
Complexity:88.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes