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CAS No. : | 504-30-3 | MDL No. : | MFCD00099605 |
Formula : | C4H4N2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | AAILEWXSEQLMNI-UHFFFAOYSA-N |
M.W : | 96.09 | Pubchem ID : | 68153 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
63% | With trichlorophosphate; | a 3-Chloropyridazine 3-(2H)-Pyridazinone (1 g, 10.4 mmol) was treated with phosphorous oxychloride (10 mL) at 90° C. for 4 H. The mixture was poured into ice (100 g), basified with 50percent NaOH, and extracted with CH2 Cl2 (3*150 mL). The combined organic extracts were dried (MgSO4) and concentrated to give the title compound as a yellow solid (750 mg, 63percent): MS (ES) m/e 115 [M+H]+. |
46% | Step A 3-(2H)-pyridazinone (5.0 g, 52.0 mmole) was treated with phosphorous oxychloride (17 ml, 179 mmole) at 85° C. for 4.5 hours. The mixture was poured into 400 g ice/H2O, basified (pH>10) with 50percent NaOH, and extracted with EtOAc (4*). The combined organic layers were washed with brine, dried (MgSO4), and concentrated. The material was run through a Hak-Pak (SiO2, 1:1 hexanes/EtOAc) to give 2.8 g (46percent) of 3-chloropyridazinone. | |
Example 130 2-Chloro-N-(1 -hydroxy-cyclohexylmethyl)-5-(pyridazin-3-yloxy)- benzamide130.1 3-Chloro-pyridazineA suspension of 3(2H)-pyridazinone (1 g) in phosphorus oxychloride (0.970 mL) was heated to 80°C for 18h. The reaction mixture was evaporated off and the residue was treated with ice 2M solution of NaOH and extracted with EtOAc. The organic phase was washed with brine, dried over MgS04 and concentrated in vacuo to give 857 mg of the crude titled compound as a purple solid.1H NMR ((CD3)2SO) delta: 9.27 (d, J = 4.7 Hz, 1 H), 7.95 (d, J = 8.7 Hz, 1 H), 7.82 (dd, 4 = 8.7 Hz, J2 = 4.7 Hz, 1 H) |
With trichlorophosphate; at 80℃; for 18h; | 130.1 3-Chloro-pyridazine A suspension of 3(2H)-pyridazinone (1 g) in phosphorus oxychloride (0.970 mL) was heated to 80° C. for 18 h. The reaction mixture was evaporated off and the residue was treated with ice 2M solution of NaOH and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give 857 mg of the crude titled compound as a purple solid. 1H NMR ((CD3)2SO) delta: 9.27 (d, J=4.7 Hz, 1H), 7.95 (d, J=8.7 Hz, 1H), 7.82 (dd, J1=8.7 Hz, J2=4.7 Hz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With trichlorophosphate; at 60℃; for 1.5h; | Preparation 118: 3-Chloro-pyridazine (Prepi 18); A mixture of pyridazin-3-ol (1.9 g, 19.8 mmol) in POCI3 (19 ml) was heated to 600C for 90 minutes. After cooling to room temperature, the reaction was quenched in ice/water and neutralized with solid NaHCO3. The product was extracted with ethyl acetate, the organic phase was washed with brine, dried (Na2SO4) and evaporated to give 2.1 g of the title compound as a brown solid (92percent yield). MS (ES) (m/z): 115.1 [M+H]+. |
67% | In trichlorophosphate; | 3-chloropyridazine A solution of 3-hydroxypyridazine (96 g, 1 mol) in phosphorous oxychloride (800 ml) is refluxed on an oil bath for 4 h. The excess amount of POCl3 is removed in vacuum, the residue is cooled and added to 2 kg of ice. The reaction mixture is then neutralized with aqueous ammonia and extracted with chloroform (4x500 ml). The combined organic extract is washed with brine (3x200 ml), dried over MgSO4 and the solvent is removed in vacuum, yielding the desired product (76 g, 67percent). |