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CAS No. : | 5004-45-5 | MDL No. : | MFCD00098272 |
Formula : | C14H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XCJLBNVENUPHEA-UHFFFAOYSA-N |
M.W : | 222.24 | Pubchem ID : | 219150 |
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 |
---|---|---|
99% | With carbazic acid; at 90℃; for 3h;Green chemistry; | General procedure: A 10.0 mmol for alpha-keto acid compound or a 5.2 mmol for beta-diketones or alpha-keto acids was mixed with 0.40 g of hydrazinium carboxylate (1a, 5.2 mmol), respectively. (For solid di-carbonyl compound, the mixture was ground using a pestle and a mortar.) The mixture was stored in a closed vial, and then heated to 70 - 90 C until the reaction was complete. Complete conversion to related product was dependent upon the nature of di-carbonyl compounds. Typically, those di-carbonyl compounds take about <3 h to complete the reactions. CO2 and water were released during the reaction. All products obtained from the reactions of 1a with di-carbonyl compounds were basically characterized by 1H and 13C NMR spectroscopy. The products have over 97% of purity of reaction mixture based on 1H NMR spectroscopy and isolation yields are over 97% based on di-carbonyl compounds. The melting points, elemental analysis and UV-Vis spectra for all azines, pyrazoles and pyridazinones, were measured after purification using appropriate solvent. |
89% | With hydrazine hydrate; In ethanol; for 6h;Reflux; | <strong>[85-52-9]2-benzoylbenzoic acid</strong> (5.66 g, 25 mmol) and 2 mL of 85% hydrazine hydrate were placed in a 150 mL round bottom flask, and then 50 mL of ethanol was added thereto and heated under reflux for 6 h. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered under reduced pressure. The solid was washed three times with a small amount of a mixed solvent of ethanol and water, and dried at 60 C for 24 hours to give 4-phenyl-1,2-dihydrophthalazine-1-one as a white solid 4.94 g, yield 89%. |
72% | With sodium hydroxide; hydrazinium sulfate; In water; for 1h;Reflux; | General procedure: A solution of hydrazine sulfate (4.0 g, 30.4 mmol) and sodium hydroxide (2.4 g, 60.8 mmol) in water (20 mL) was heated on a steam bath for 20 min, then the latter was added to solution of 8a, b (30.4 mmol) in water (20 mL). The reaction mixture was heated under reflux for 1 h, upon cooling the residue obtained was filtered, washed with water and crystallized from propanol to obtain the desired compounds 9a, b, respectively [32]. |
With hydrazine hydrate; In ethanol; for 3h;Reflux; | General procedure: 2-Acetyl or <strong>[85-52-9]2-benzoylbenzoic acid</strong> derivatives (0.01 mol) and hydrazine hydrate (0.01 mol) in 30 mL of ethanol were refluxed for 3 hours. At the end of this period, the reaction mixture was cooled and the resulting precipitate was filtered to give compounds 2 and 3 respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tetraphosphorus decasulfide; triethylamine In acetonitrile for 1h; Reflux; | |
Multi-step reaction with 2 steps 1: trichlorophosphate; <i>N</i>,<i>N</i>-dimethyl-aniline / 100 - 105 °C 2: cyclohexylaminodithiocarboxylic acid, cyclohexylammonium salt / chloroform / 12 h / 61 °C | ||
With tetraphosphorus decasulfide; xylene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 33% | With hydrogenchloride In ethanol for 36h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride 1.) DMF, 110 deg C, 2.) DMF; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride 1.) DMF, 110 deg C, 2.) DMF; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium ethanolate In ethanol for 2h; Heating; | |
75% | With potassium carbonate In N,N-dimethyl-formamide for 24h; Reflux; | |
66.4% | With potassium carbonate In acetone for 30h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-benzyl-trimethylammonium hydroxide In 1,4-dioxane at 120℃; for 3h; Yield given; | ||
With N-benzyl-trimethylammonium hydroxide In ethanol for 8h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With trichlorophosphate In acetonitrile Reflux; Inert atmosphere; | |
80% | With trichlorophosphate In chloroform Reflux; | 1.2 Preparation of 1-chloro-4-phenylphthalazine A solution of 4-phenyl-2,3-dihydrophtalazine-1-one (4.44 g, 20 mmol) in step (1), 10 mL of phosphorus oxychloride and 50 mL of dry chloroform was placed in a round bottom flask , Heated to reflux to clarify the solution, And the reaction was complete with n-hexane-ethyl acetate (1:1, volume ratio). (NaOH solution, then add the right amount of NaHCO3), standing, extracted with dichloromethane to collect (1 mL), then add the appropriate amount of NaHCO3, and then add the appropriate amount of NaHCO3), the mixture was poured into ice water, The organic phase. The solvent was removed by evaporation under reduced pressure, and the residue was recrystallized from ethanol to give 3.85 g of 1-chloro-4-phenylphthalazine in a yield of 80%. |
79% | With trichlorophosphate at 85℃; for 4h; |
77% | With trichlorophosphate for 5h; Heating; | |
73% | With trichlorophosphate at 85℃; for 4h; | |
65% | With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline for 6h; Reflux; | |
With trichlorophosphate Heating; | ||
With phosphorus pentachloride; trichlorophosphate Heating; | ||
With trichlorophosphate | ||
With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate at 100 - 105℃; | General method for the preparation of heterocyclic thioamides General procedure: Method B. To a cold solution of heterocyclic amide (2.5 mmol)in POCl3 (25 mL) was added dimethylaniline (2.5 mmol). Thereaction mixture was stirred under reflux (100-105 °C) for1.5-2 h. The excess POCl3 was removed under reduced pressure. The residue was poured into a mixture of chloroform(50 mL), ice water (80 mL) and ammonia (5 mL). The chloroform layer was separated, dried over Na2SO4 and filtered. Tothis chloroform solution of the in situ generated chloroheterocycles was added (0.69 g, 2.5 mmol) of N-cyclohexyl dithiocarbamate cyclohexylammonium salt. The reaction mixture was refluxed at 61 °C for 12 h. The reaction mixture was evaporatedunder reduced pressure and 25 mL of ethanol was added to thesolid residue. The yellowish-orange precipitate was filtered togive the desired product. The crude compounds were pureenough for analytical purposes. Purification of products foranalysis was achieved by crystallization from the appropriatesolvent; chromatographed with the appropriate eluent or byrepeated dissolution in KOH and reprecipitation by acetic acid. | |
With trichlorophosphate In N,N-dimethyl-formamide | ||
With trichlorophosphate Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride; hydrogen 1.) THF, reflux, 1 h, 2.) ethanolic HCl, 45-53 deg C, 4 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With hydrazine hydrate In N,N-dimethyl-formamide for 20h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrazine hydrate In propan-1-ol at 100℃; for 16h; Inert atmosphere; | |
68% | With hydrazine hydrate In acetic acid for 4h; Heating; | |
With hydrazine hydrate In propan-1-ol Heating; |
With hydrazine hydrate In propan-1-ol at 97℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In toluene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In diethyl ether; benzene for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With aluminium trichloride Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With hydrogenchloride; zinc for 1h; Heating; | |
With hydrogenchloride; zinc |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrazine hydrate at 100℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 4-phenyl-2H-phthalazin-1-one With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 4-(2-bromoethyloxy)benzaldehyde In N,N-dimethyl-formamide at 65 - 70℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrazine at 100℃; for 2h; | 4 A mixture of 2-benzoyl-benzoic acid N',N'-dimethyl-hydrazide 17 (1 mmol) and H2ννH2*H2O (18 mmol) was stirred for 2 hrs at 100 0C. After the excess hydrazine was removed under reduced pressure, the crude product was purified by chromatography on silica gel ((1:2) EtOAc:hexane) to give the desired product in 95% yield.1H NMR (300 MHz, CDCl3) δ (ppm): 11.10 (s, NH), 8.67 (d, J=3.9Hz, IH), 7.94-7.90 (m, 3H), 7.72-7.64 (m, 5H). 13C NMR (75 MHz, CDCl3) δ (ppm): 162.2, 150.1, 136.8, 135.2, 133.4, 131.5, 131.2, 131.0, 130.4, 130.2, 129.3, 128.8, 128.7, 127.6. |
95% | With hydrazine hydrate at 100℃; for 2h; | A mixture of 2-benzoyl-benzoic acid N',N'-dimethyl-hydrazide 17 (1 mmol) and H2NNH2.H2O (18 mmol) was stirred for 2 hrs at 100° C. After the excess hydrazine was removed under reduced pressure, the crude product was purified by chromatography on silica gel ((1:2) EtOAc:hexane) to give the desired product in 95% yield.1H NMR (300 MHz, CDCl3) δ (ppm): 11.10 (s, NH), 8.67 (d, J=3.9 Hz, 1H), 7.94-7.90 (m, 3H), 7.72-7.64 (m, 5H). 13C NMR (75 MHz, CDCl3) δ (ppm): 162.2, 150.1, 136.8, 135.2, 133.4, 131.5, 131.2, 131.0, 130.4, 130.2, 129.3, 128.8, 128.7, 127.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With titanium tetrachloride; methoxybenzene In dichloromethane at 100℃; for 1h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: K2CO3 / dimethylformamide / 0.5 h / 25 °C 1.2: 85 percent / dimethylformamide / 24 h / 65 - 70 °C 2.1: 87 percent / piperidine; benzoic acid / toluene / 1 h / Heating 3.1: 60 percent / H2 / 10 percent Pd/C / dioxane / 20 °C / 3102.89 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: K2CO3 / dimethylformamide / 0.5 h / 25 °C 1.2: 85 percent / dimethylformamide / 24 h / 65 - 70 °C 2.1: 87 percent / piperidine; benzoic acid / toluene / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 49 percent / Zn; aq. HCl / 1 h / Heating 2.1: NaH / tetrahydrofuran / 2 h / Heating 2.2: 26 percent / tetrahydrofuran / 5 h / Heating | ||
Multi-step reaction with 2 steps 1: Zn; HCl 2: NaH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 49 percent / Zn; aq. HCl / 1 h / Heating 2.1: NaH / tetrahydrofuran / 2 h / Heating 2.2: 26 percent / tetrahydrofuran / 5 h / Heating 3.1: 40 percent / acetonitrile / 72 h / 20 °C | ||
Multi-step reaction with 3 steps 1: Zn; HCl 2: NaH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 79 percent / POCl3 / 4 h / 85 °C 2: 61 percent / NH4Cl / butan-1-ol / 48 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 73 percent / ethanol / 2 h / Heating 2: 57 percent / diethyl ether; benzene / 6 h / Heating | ||
Multi-step reaction with 2 steps 1: 73 percent / ethanol / 2 h / Heating 2: 68 percent / AlCl3 / Ambient temperature | ||
Multi-step reaction with 2 steps 1: AlCl3 / 5 h / Heating 2: concd aq. HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylbenzylammonium hydroxide (Triton B) / ethanol / 8 h / Heating 2: 89 percent / Et3N, H2, pyridine / 48 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 1 h / 60 °C 2: K2CO3 / dimethylformamide / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 1 h / 60 °C 2: K2CO3 / dimethylformamide / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 1 h / 60 °C 2: K2CO3 / dimethylformamide / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 1 h / 60 °C 2: K2CO3 / dimethylformamide / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 1 h / 60 °C 2: K2CO3 / dimethylformamide / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 1 h / 60 °C 2: K2CO3 / dimethylformamide / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 110 deg C, 2.) DMF 2: LiOH*H2O, H20 / methanol / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 110 deg C, 2.) DMF 2: LiOH*H2O, H2O / methanol / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 54 percent / tetrahydrofuran; cyclohexane; diethyl ether / -40 deg C, 40 min, room temp., 17 h 2: 49 percent / hydrazine hydrate / dimethylformamide / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 54 percent / tetrahydrofuran; cyclohexane; diethyl ether / -40 deg C, 40 min, room temp., 17 h 2: 49 percent / hydrazine hydrate / dimethylformamide / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) LiAlH4, 2.) H2 / 2.) 10percent Pd/C / 1.) THF, reflux, 1 h, 2.) ethanolic HCl, 45-53 deg C, 4 h 2: 89 percent / H2 / Raney nickel / methanol / 6 h / 49 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3 / Heating 2: 53 percent / ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3 / Heating 2: 53 percent / ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Triton-B (40percent in methanol) / dioxane / 3 h / 120 °C 2: 10percent aq. KOH / 7 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / NaOC2H5 / ethanol / 2 h / Heating 2: 75 percent / hydrazine hydrate / ethanol / 3 h / Heating 3: 75 percent / 1 h / 200 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / NaOC2H5 / ethanol / 2 h / Heating 2: 75 percent / hydrazine hydrate / ethanol / 3 h / Heating | ||
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 30 h / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 80 percent / NaOC2H5 / ethanol / 2 h / Heating 2: 75 percent / hydrazine hydrate / ethanol / 3 h / Heating 3: 70 percent / DMF / 4 h / Heating 4: 60 percent / sodium ethylate / ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / NaOC2H5 / ethanol / 2 h / Heating 2: 75 percent / hydrazine hydrate / ethanol / 3 h / Heating 3: 75 percent / potassium hydroxide / ethanol / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / NaOC2H5 / ethanol / 2 h / Heating 2: 75 percent / hydrazine hydrate / ethanol / 3 h / Heating 3: 70 percent / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium hydroxide In tetrahydrofuran; methanol; ethanol; water | 194 2-Aminomethyl-α-phenylbenzenemethanamine EXAMPLE 194 2-Aminomethyl-α-phenylbenzenemethanamine To a slurry of 3.8 g (100 mmol) of lithium aluminium hydride in 120 mL of THF was added 11.1 g (50 mmol) of 4-phenyl-1(2H)phthalazinone. The mixture was refluxed one hour, cooled, diluted with 100 mL of ether and sequentially treated with 3.8 mL of water, 3.8 mL of 15% aqueous sodium hydroxide and 11.4 mL of water. The mixture was stirred for 30 minutes and the granular precipitate filtered off. The filtrate was diluted with a little toluene, dried over sodium sulfate and stripped to provide 14.1 g of an oil which was dissolved in 180 mL of ethanol and hydrogenated at 50 psi in the presence of 20 mL of ethanolic HCl and 1.5 g of 10% palladium on carbon. After 24 hours a precipitate had formed. The reaction was filtered, the precipitate was slurried in 250 mL of hot methanol and filtered again. The combined filtrates were stripped to about 100 mL and diluted with ether. On cooling, 7.3 g of 1,2,3,4-tetrahydro-1-phenylphthalazine as the monohydrochloride salt was filtered off. It was recrystallized from methanol/ether to provide 6.93 g (56%) of product, mp 251-253. The tetrahydrophthalazine was redissolved in 200 mL of methanol by warming and hydrogenated at 50 psi at 66° for 20 hours in the presence of 3.5 g of Raney nickel catalyst. The catalyst was filtered off and the filtrate stripped. The residue was recrystallized from methanol/ether to provide 99% yield of the diamine dihydrochloride salt, mp 270-273. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
278 2-[2-(4-Nitrophenyl)ethyl]-4-phenyl-1(2H)-phthalazinone EXAMPLE 278 2-[2-(4-Nitrophenyl)ethyl]-4-phenyl-1(2H)-phthalazinone (Formula VIII: R2 = STR256 R5 =Ph, R6 =H) By a procedure analogous to that of Example 186, 11.8 g of 2-[2-(4-nitrophenyl)ethyl]-4-phenyl-1(2H)-phthalazinone was prepared from 10.0 g (45 mmol) of 4-phenyl-1(2H)-phthalazinone and 11.6 g (50 mmol) of 4-nitrophenethyl bromide. The product was recrystallized from EtOAc-ether-hexane, mp 152°-155°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hydrogencarbonate; trichlorophosphate In para-xylene | 1 Preparation of 1-neopentylamino-4-phenylphthalazine EXAMPLE 1 Preparation of 1-neopentylamino-4-phenylphthalazine To a suspension of 100 g of 4-phenyl-1(2H)-phthalazinone and 96.2 g of neopentylamine in 300 ml of p-xylene were added dropwise 83.7 g of phosphorus oxychloride with stirring and the resulting mixture was stirred under reflux for 4 hours. After allowing to be cooled, a saturated aqueous solution of NaHCO3 was added to the reaction mixture. Then, the mixture was extracted with chloroform and the organic layer was separated, dried and then concentrated. The residue was recrystallized from ethanol to afford the title compound as a pale yellow crystal. 100.8 g (Yield, 77%) Melting point: 215.5°-216.5° C. Infrared spectrum: 3240, 2950, 1570, 1515, 775, 695 cm-1. Mass spectrum: 291 (M+), 276, 261, 234, 220, 205, 77. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium methylate In methanol for 6h; Reflux; | |
65% | Stage #1: 4-phenyl-2H-phthalazin-1-one With sodium methylate In methanol for 0.5h; Heating / reflux; Stage #2: (2-chloroethyl)dimethylamine hydrochloride In methanol for 6h; Heating / reflux; | 1 To the solution of sodium methoxide (0,0148 mol of Na) in dry methanol (20 ml) was added 4-phenyl-2H-phthalazin-l-on (0,0070 mol). The mixture was stirred and refluxed for 30 minutes, then cooled to ambient temperature and (2-chloroethyl)- dimethylammonium chloride was added. Afterwards the reaction mixture was heated and refluxed for 6 hours. After cooling to room temperature, the inorganic material was collected by filtration and the filtrate was evaporated to dryness. The residue was triturated with hydrochloric acid (20 ml, c = 2 mol/dm3). The filtrate was neutralised with aqueous solution of sodium hydroxide and extracted with dichloromethane (3x20ml). The combined extracts were dried over anhydrous MgSO4 and vacuum concentrated till dryness. The residue was subjected to column chromatography (silica gel, eluent: MeOH - ethyl acetate = 1 : 1)2-[2-(Dimethylamino)ethyl]-4-phenyl-2H-phthalazin-l-one (compound no. 1)Yield 65%;Elemental Analysis:Calculated for C18H19N3O M = 293. 37 g/mol: C 73.70, H 6.53,N 14.32;Found: C 73.52; H 6.55, N 14.29. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: 4-phenyl-2H-phthalazin-1-one With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at -10℃; for 0.25h; Inert atmosphere; Stage #2: methyl(2-hydroxyethyl)carbamic acid tert-butyl ester In tetrahydrofuran; toluene at -10 - 20℃; for 22h; Inert atmosphere; | General Procedure for Preparation of Acetyl- and tert-Butoxycarbonyl- Derivatives of 2-[(Methylamino)ethyl]-2H-phthalazin-1-ones 11 (Mitsunobu Procedure) General procedure: The Mitsunobu reaction was carried out under argon. To a stirred solution of TPP (0,0102 mol) in dry THF (10 ml) was slowly added DEAD (0,0102 mol, solution in toluene c ≈ 40%) at -10°C. Then a solution of phthalazinone 1 (0.0068 mol) in THF (44 ml) was added dropwise. The whole lot was mixed for 15 min at -10°C and next was added the appropriate derivative of N-methylethanolamine 7 or 8 (0.00748 mol) in THF (5 ml) at -10°C. The mixture was stirred during 2 hrs at -10°C, after which time, the reaction mixture was warmed to ambient temperature and stirred in this conditions for 20 hrs. All volatile materials were removed under reduced pressure, ethyl ether (20ml) was added to the residue and the whole lot was stirred for 0.5 hrs at ambient temperature. The separate white solid was collected by flirtation, washed with ether and filtrate was evaporated to dryness. The residue was subjected to column chromatography to give the pure product 11. |
50% | Stage #1: 4-phenyl-2H-phthalazin-1-one With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at -10℃; for 0.25h; Stage #2: methyl(2-hydroxyethyl)carbamic acid tert-butyl ester In tetrahydrofuran; toluene at -10 - 20℃; for 22h; | 6 The reaction was performed in atmosphere of argon. To triphenyphosphine (0.0102 mol) stirred in THF (10 ml) at -1O0C the solution of diethyl azodicarboxylate (0.0102 mol, c « 40%) in toluene was added dropwise, followed by the solution of phthalazinone (0.0068 mol) in THF (44 ml). After 15 minutes at -1O0C the solution of corresponding N-acyl-derivative of N-methylethanoloamine (0.00748 mol) in THF (5 ml) was added. The reaction mixture after 2 hours at -1O0C was warmed up to ambient temperature and kept at this temperature for 20 hours with vigorous stirring. Then all volatile materials were removed under reduced pressure and to the residue diethyl ether (20 ml) was added. The mixture was stirred at ambient temperature for 20 minutes. Afterwards the white solid was filtered off and the filtrate was concentrated and subjected to column chromatography. The product was purified by crystallization.Methyl-[2-(l-oxo-4-phenyl-lH-phthalazin-2-yl)-ethyl]-carbamic acid tert-butyl ester (compound no. 10)Yield 50%;Elemental Analysis:Calculated for C22H25N3O3 M = 279. 46 g/mol: C 69.64, H 6.64, N 11.07;Found: C 69.57; H 6.77, N 11.09. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 37 %Chromat. 2: 32 %Chromat. 3: 3 %Chromat. | With acetic acid In methanol at 15℃; for 4.66667h; Electrochemical reaction; | |
1: 2 %Chromat. 2: 51 %Chromat. 3: 3 %Chromat. | With acetic acid In methanol at 15℃; for 4.66667h; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With O-(diphenylphosphinyl)hydroxylamine; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 3h; | g.17.17B Example 17B2-amino-4-phenylphthalazin-1(2H)-oneA mixture of 4-phenylphthalazin-1(2H)-one (Aldrich) (500 mg, 2.25 mmol) and KOtBu (3.37 mL, 3.37 mmol) was stirred for 45 minutes, diluted with DMF for solubility, and Example 17A (787 mg, 3.37 mmol) was added and stirred for 3 hours. The mixture was diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to give 509 mg (95%) of the title compound. MS (DCI/NH3) m/z 238 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-phenyl-2H-phthalazin-1-one With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1-iodo-3-chloro-propane In N,N-dimethyl-formamide for 1h; | 2-(3-chloropropyl)-4-(3,4-difluorophenyl)phthalazin-1(2H)-one (9n) General procedure: 335 mg (1.30 mmol) of 4-(3,4-difluorophenyl)phthalazin-1(2H)-one (8n) was dissolved in 10 ml of N,N-dimethylformamide, and 62 mg (1.56 mmol) of sodium hydride were added at 0oC. After being stirred for 30 min, 0.21 ml (1.95 mmol) 3-iodo-1-chloropropane was then added to reaction mixture. After being stirred for 1 h, the reaction mixture was combined with 50 ml of water and extracted with ethylacetate (50 ml X 2) being washed with water and a sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (ethyl acetate : n-hexane = 1 : 3) to obtain 400 mg (yield 92%) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 90℃; for 3h;Sealed tube; Molecular sieve; | General procedure: To a stirred mixture of 2-bromobenzaldehyde (0.5 mmol) and the corresponding hydrazinehydrochloride (0.6 mmol) in DMF taken in a 25 mL sealed tube, was added Pd(OAc)2 (5 mol %), dppf (6 mol %), molecular sieves (W/W), DBU (1.25 mmol), and Co2(CO)8 (0.15 mmol). The reaction vessel was closed immediately and heated at 90 C for 3 h. The reaction mixture was cooled to room temperature, filtered through celite bed. The filtrate was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine solution, dried over MgSO4, evaporated in vacuum and purified using column chromatography on silica gel (60-120 mesh) to afford the pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: 2-chloro-N-(4-sulfamoylphenyl)acetamide With potassium carbonate In acetone for 1h; Reflux; Stage #2: 4-phenyl-2H-phthalazin-1-one In acetone for 12h; Reflux; | Method A General procedure: To a solution of the appropriate amides 7a-e (2 mmol) in acetone (20 mL), K2CO3 (0.69 g, 5 mmol) was added and reflux for 1 h. For this solution, the appropriate phthalazin-1(2H)-ones 9a, b or 14a, b (2mmol) was added and the reflux was continued for 12 h, then left to cool at room temperature and poured into cursed ice. The resulted precipitate was filtered, dried and then recrystallized from DMF/H2O to afford the targeted compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: 4-phenyl-2H-phthalazin-1-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2‐chloro‐N‐(4‐(N‐(thiazol‐2‐yl)sulfamoyl)phenyl)acetamide In N,N-dimethyl-formamide for 8h; Reflux; | Method B General procedure: To a stirred solution of the appropriate phthalazin-1(2H)-one 14a, b (10 mmol) in dry DMF (20 mL), NaH (60%) (0.4 g, 10 mmol) was added and stirred for 30 min at room temperature. After that the appropriate intermediates 7a-e (10 mmol) were added at room temperature then reflux for 8 h, then left to cool, poured into crushed ice the obtained precipitate, then filtered and washed with dioxan and recrystallization from DMF/H2O gave the targeted compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: 4-phenyl-2H-phthalazin-1-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-chloro-N-{4-[(pyrimidin-2-ylamino)sulfonyl]phenyl}acetamide In N,N-dimethyl-formamide for 8h; Reflux; | Method B General procedure: To a stirred solution of the appropriate phthalazin-1(2H)-one 14a, b (10 mmol) in dry DMF (20 mL), NaH (60%) (0.4 g, 10 mmol) was added and stirred for 30 min at room temperature. After that the appropriate intermediates 7a-e (10 mmol) were added at room temperature then reflux for 8 h, then left to cool, poured into crushed ice the obtained precipitate, then filtered and washed with dioxan and recrystallization from DMF/H2O gave the targeted compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate / acetonitrile / Reflux; Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: pyridine / acetonitrile / 0.17 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: 4-phenyl-2H-phthalazin-1-one With sodium methylate In methanol for 0.5h; Heating; Stage #2: toluene-4-sulfonic acid 2-[methyl-(toluene-4-sulfonyl)-amino]-ethyl ester In methanol for 7h; Heating; | General Procedure for Preparation of Benzenesulfonamides 9 General procedure: To a solution of sodium methoxide (0.0165 mol) in dry MeOH (70 ml) was added 2H-phthalazin-1-one 1 (0.0153 mol). The mixture was heated to boiling for 30 minutes. Afterwards, toluene-4-sulfonic acid 2-[methyl-(toluene-4-sulfonyl)-amino]-ethyl ester (6) (0.0230 mol) was added and heating was continued for next 7 hrs. After this time, the mixture was cooled to ambient temperature. The separated product was filtrated off, washed with dry methanol and purified by crystallization or column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 4-phenyl-2H-phthalazin-1-one With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at -10℃; for 0.25h; Inert atmosphere; Stage #2: N-(2-hydroxyethyl)-N-methylethanamide In tetrahydrofuran; toluene at -10 - 20℃; for 22h; Inert atmosphere; | General Procedure for Preparation of Acetyl- and tert-Butoxycarbonyl- Derivatives of 2-[(Methylamino)ethyl]-2H-phthalazin-1-ones 11 (Mitsunobu Procedure) General procedure: The Mitsunobu reaction was carried out under argon. To a stirred solution of TPP (0,0102 mol) in dry THF (10 ml) was slowly added DEAD (0,0102 mol, solution in toluene c ≈ 40%) at -10°C. Then a solution of phthalazinone 1 (0.0068 mol) in THF (44 ml) was added dropwise. The whole lot was mixed for 15 min at -10°C and next was added the appropriate derivative of N-methylethanolamine 7 or 8 (0.00748 mol) in THF (5 ml) at -10°C. The mixture was stirred during 2 hrs at -10°C, after which time, the reaction mixture was warmed to ambient temperature and stirred in this conditions for 20 hrs. All volatile materials were removed under reduced pressure, ethyl ether (20ml) was added to the residue and the whole lot was stirred for 0.5 hrs at ambient temperature. The separate white solid was collected by flirtation, washed with ether and filtrate was evaporated to dryness. The residue was subjected to column chromatography to give the pure product 11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | Stage #1: 4-phenyl-2H-phthalazin-1-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.75h; Inert atmosphere; Stage #2: 2-(2-bromoethyl)isoindoline-1,3-dione In N,N-dimethyl-formamide at 0 - 20℃; for 21h; Inert atmosphere; | General Procedure for Preparation of 2-[2-(1-Oxo-1H-phthalazin-2-yl)-ethyl]-isoindole-1,3-diones 3 General procedure: The reaction was carried out under argon. To a stirred suspension of sodium hydride (4.25 mol) in dry DMF (10 cm3) was added slowly a solution of 2H-phthalazin-1-one 2 (3.95×10-3 mol) in dry DMF (50 cm3). The reaction mixture was stirred at room temperature for 45 minutes. Next, the whole lot was cooled to 0 ° C and the solution of N-(2-bromoethyl)phthalimide (5.92×10-3 mol) in dry DMF (10 cm3) was added in portions. At first the mixture was kept for 5 hours in 0 ° C and later for 16 hours in ambient temperature. After this time the reaction mixture was poured into ice-water mixture (100 cm3) and next extracted with CHCl3 (3×50 cm3). The combined extracts were dried over MgSO4 and concentrated under vacuum. The isoindole-1,3-dione 3 was isolated by column chromatography or crystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate / 4 h / 85 °C 2: isopropyl alcohol / 4 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 7 h / Reflux 2: bromine / tetrachloromethane / 3.5 h / 20 °C | ||
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 24 h / Reflux 2: bromine / tetrachloromethane / 3.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / Reflux 2: triethylamine; water / methanol / 20 °C | ||
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C 2: triethylamine; water / methanol / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 20 °C 2.1: triethylamine; water / methanol / 20 °C | ||
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C 2: triethylamine; water / methanol / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In acetone for 7h; Reflux; | |
75% | With potassium carbonate In acetone for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium carbonate In acetone for 7h; Reflux; | |
62% | With potassium carbonate In acetone for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With potassium carbonate In N,N-dimethyl-formamide | |
53% | With potassium carbonate In N,N-dimethyl-formamide for 15h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With potassium carbonate In N,N-dimethyl-formamide for 10h; Reflux; | |
35% | With potassium carbonate In N,N-dimethyl-formamide for 15h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In N,N-dimethyl-formamide for 2h; Reflux; | |
98% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 4-phenyl-2H-phthalazin-1-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-acetoxyethoxymethyl bromide In N,N-dimethyl-formamide at 20℃; | |
60% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at -10℃; for 0.25h; | General procedure for the preparation of electron-poor Nvinylatedphthalazinone and 5,5-diphenylimidazolidine-2,4-dione General procedure: To a magnetically stirred solution of triphenylphosphine(0.262 g, 1 mmol) and a NH-acid derivative (1 mmol) indichloromethane (5 mL) was added dropwise a mixture of aacetylenic ester (1 mmol) in dichloromethane (2 mL) at -10°Cover 15 min. The mixture was allowed to warm up to roomtemperature and stirred for 48 h at room temperature. Thesolvent was removed under reduced pressure and the viscousresidue was purified by flash column chromatography (silica gel;petroleum ether-ethyl acetate). The solvent was removed underreduced pressure and the products were obtained. The characterizationdata of the compounds are given below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at -10℃; for 0.25h; | General procedure for the preparation of electron-poor Nvinylatedphthalazinone and 5,5-diphenylimidazolidine-2,4-dione General procedure: To a magnetically stirred solution of triphenylphosphine(0.262 g, 1 mmol) and a NH-acid derivative (1 mmol) indichloromethane (5 mL) was added dropwise a mixture of aacetylenic ester (1 mmol) in dichloromethane (2 mL) at -10°Cover 15 min. The mixture was allowed to warm up to roomtemperature and stirred for 48 h at room temperature. Thesolvent was removed under reduced pressure and the viscousresidue was purified by flash column chromatography (silica gel;petroleum ether-ethyl acetate). The solvent was removed underreduced pressure and the products were obtained. The characterizationdata of the compounds are given below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at -10℃; for 0.25h; | General procedure for the preparation of electron-poor Nvinylatedphthalazinone and 5,5-diphenylimidazolidine-2,4-dione General procedure: To a magnetically stirred solution of triphenylphosphine(0.262 g, 1 mmol) and a NH-acid derivative (1 mmol) indichloromethane (5 mL) was added dropwise a mixture of aacetylenic ester (1 mmol) in dichloromethane (2 mL) at -10°Cover 15 min. The mixture was allowed to warm up to roomtemperature and stirred for 48 h at room temperature. Thesolvent was removed under reduced pressure and the viscousresidue was purified by flash column chromatography (silica gel;petroleum ether-ethyl acetate). The solvent was removed underreduced pressure and the products were obtained. The characterizationdata of the compounds are given below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at -10℃; for 0.25h; | General procedure for the preparation of electron-poor Nvinylatedphthalazinone and 5,5-diphenylimidazolidine-2,4-dione General procedure: To a magnetically stirred solution of triphenylphosphine(0.262 g, 1 mmol) and a NH-acid derivative (1 mmol) indichloromethane (5 mL) was added dropwise a mixture of aacetylenic ester (1 mmol) in dichloromethane (2 mL) at -10°Cover 15 min. The mixture was allowed to warm up to roomtemperature and stirred for 48 h at room temperature. Thesolvent was removed under reduced pressure and the viscousresidue was purified by flash column chromatography (silica gel;petroleum ether-ethyl acetate). The solvent was removed underreduced pressure and the products were obtained. The characterizationdata of the compounds are given below. |
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