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CAS No. : | 4114-31-2 | MDL No. : | MFCD00007595 |
Formula : | C3H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | H2NNHC(O)OCH2CH3 | InChI Key : | VYSYZMNJHYOXGN-UHFFFAOYSA-N |
M.W : | 104.11 | Pubchem ID : | 20064 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P405 | UN#: | 2811 |
Hazard Statements: | H301-H315-H319 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; | EXAMPLE 1 Ethyl 2-[6-[ethyl-(2-hydroxypropyl)amino]-3-pyridazinyl]hydrazinecarboxylate (4) (cadralazine) To 583 g (3.91 moles) of melted 3,6-dichloropyridazine (I) (at about 70) was added under nitrogen and stirring over 6 h 1 liter (8.67 moles) of N-ethyl-N'-(2-hydroxypropyl)amine (2). The mixture was stirred at 95 for 16 h. After cooling to 40, 1.5 liters of water, 470 ml of 37% (w/w) hydrochloric acid and 884 ml (8.49 moles) of ethyl hydrazinecarboxylate were added. The solution was refluxed under nitrogen for 20 h. After cooling to room temperature the mixture was brought to pH 8.5 with 32% (w/w) ammonium hydroxide. The mixture was maintained at 0 overnight, then filtered. The precipitate was washed with cold water until elimination of chloride ions. Crystallisation from ethanol 95% afforded 776 g (70%) of the title compound m.p. 165. | |
With hydrogenchloride; In water; | Example 1 Ethyl 2-[6-[ethyl-(2-hydroxypropyl)amino]-3-pyridazinyl]-hydrazinecarboxylate (4) (cadralazine) To 583 g (3.91 moles) of melted 3,6-dichloropyridazine (I) (at about 70) was added under nitrogen and stirring over 6h 1 litre (8.67 moles) of N-ethyl-N'-(2-hydroxypropyl)amine (2). The mixture was stirred at 95 for 16h. After cooling to 40, 1.5 litres of water, 470 ml of 37% (w/w) hydrochloric acid and 884ml (8.49 moles) of ethyl hydrazinecarboxylate were added. The solution was refluxed under nitrogen for 20h. After cooling to room temperature the mixture was brought to pH 8.5 with 32% (w/w) ammonium hydroxide. The mixture was maintained at 0 overnight, then filtered. The precipitate was washed with cold water until elimination of chloride ions. Crystallisation from ethanol 95% afforded 776g (70%) of the title compound m.p. 165. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 20℃; | General procedure: A mixture of hydrzinecarboxylate 10 (0.13 g,1.0 mmol) and isatin 9 (1.0 mmol) inethyl alcohol (10 mL) was stirred at room temperature for 2-5 h and monitoredby TLC. After complete consumption of the starting compounds, resulting solidwas filtered off, washed with ethylalcoholand dried. |
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