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CAS No. : | 64362-32-9 | MDL No. : | MFCD00209545 |
Formula : | C13H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 227.22 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
61% | With aluminium trichloride at 80℃; for 6h; | |
With aluminium trichloride | ||
With aluminium trichloride for 4h; Heating; |
With aluminium trichloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium permanganate; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
beim Erhitzen auf den Schmelzpunkt; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With toluene-4-sulfonic acid In toluene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate 1.) water, 2.) DMF, 0 deg C, 5 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diphenyl-phosphinic acid; triethylamine 1.) benzene, reflux, 1 h, 2.) H2O, 1 h, heating; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride In benzene for 0.666667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With hydrazine hydrate In ethanol for 1h; Heating; | |
71% | With hydrazine In ethanol; water for 3h; Heating / reflux; | 36.1 To a round bottomed flask containing 3-benzoylpicolinic acid (2.00 g, 9 mmol) was added 50 mL of ethanol. Hydrazine hydrate (0.6 ml, 11 mmol) was added and the mixture was heated to reflux for 3h. After cooling to rt, the solvent was removed in vacuo. The resulting yellow solid was recrystallized from 30 mL of boiling 1-propanol to afford 5- phenylpyrido[2,3-d]pyridazin-8(7H)-one 70 (1.4g, 71% yield) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 10.55 (br s, IH), 9.16 (dd, J= 8.6, 1.6 Hz, IH), 7.73 (dd, J= 8.6, 4.7 Hz, IH), 7.56 (m, 5H). |
62% | With hydrazine hydrate; acetic acid for 2h; Heating; |
Multi-step reaction with 2 steps 1: 88 percent / hydroxylamine hydrochloride; pyridine / 0.5 h / Heating 2: hydrazine hydrate; acetic acid / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfuric acid for 0.75h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfuric acid for 0.75h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran for 0.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Geschw.-konst. d. Decarboxylierung; | ||
Decarboxylierung: Geschw.-konst. (Tab. 5, S.1103); | ||
Erhitzen (2 h, Siedetemp.) m. Kaliumpersulfat in wss. NaOH bei pH 7-9 fuehrt zu 4-Aza-fluorenon; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 270℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | 1.a a a 3-benzoylpyridine-2-carboxylic acid 10 g (67 mmol) quinolinic acid anhydride was suspended in 50 ml benzene and 17.9 g (134 mmol) AlCl3 was added in portions while cooling on ice. After completion of the addition, it was stirred for a further 3 hours at room temperature, carefully admixed with ice and aspirated from the precipitate which was present. The crude product was purified by column chromatography on silica gel 60 using ethyl acetate/dichloromethane 1/1 as the eluent. Yield 3.5 g (23% of theoretical yield) | |
Chinolinsaeureanhydrid, 1.) sd. Bzl., Friedel-Crafts-Rk., 2.) Faellung d. Kupferchelats, 3.) Zers. d. Kupferchelats m. H2S; | ||
(yield)53 percent (vgl. Zitat); |
Chinolinanhydrid; | ||
there are obtained the following respective compounds: ... 2-(3- trifluoromethylbenzoyl)-3-carboxypyridine and 2-carboxy-3-(3- trifluoromethylbenzoyl)pyridine; 2-(3,4 -methylenedioxybenzoyl)-3-carboxypyridine and 2-carboxy-3-(3,4-methylenedioxybenzoyl)pyridine; 2-(3-methoxybenzoyl)-3-carboxypyridine and 2-carboxy-3-(3-methoxybenzoyl)pyridine; 2-benzoyl-3-carboxypyridine and 2-carboxy-3-benzoylpyridine; and 2-benzoyl-3-carboxypyridine and 2-carboxy-3-benzoylpyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With pyridine; hydroxylamine hydrochloride for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / benzene / 0.67 h / Heating 2: triethylamine / dioxane / 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / benzene / 0.67 h / Heating 2: triethylamine / dioxane / 24 h 3: 80 percent / HCl (g) / dioxane; diethyl ether / 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 62 percent / hydrazine hydrate; acetic acid / 2 h / Heating 2: 78 percent / phosphorus oxychloride; pyridine / 1 h / 110 °C | ||
Multi-step reaction with 3 steps 1: 88 percent / hydroxylamine hydrochloride; pyridine / 0.5 h / Heating 2: hydrazine hydrate; acetic acid / Heating 3: 78 percent / phosphorus oxychloride; pyridine / 1 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 62 percent / hydrazine hydrate; acetic acid / 2 h / Heating 2: 78 percent / phosphorus oxychloride; pyridine / 1 h / 110 °C 3: 68 percent / hydrazine hydrate / ethanol / 1 h / Heating | ||
Multi-step reaction with 4 steps 1: 88 percent / hydroxylamine hydrochloride; pyridine / 0.5 h / Heating 2: hydrazine hydrate; acetic acid / Heating 3: 78 percent / phosphorus oxychloride; pyridine / 1 h / 110 °C 4: 68 percent / hydrazine hydrate / ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 62 percent / hydrazine hydrate; acetic acid / 2 h / Heating 2: 78 percent / phosphorus oxychloride; pyridine / 1 h / 110 °C 3: 68 percent / hydrazine hydrate / ethanol / 1 h / Heating 4: 82 percent / 12 h / 45 - 50 °C | ||
Multi-step reaction with 5 steps 1: 88 percent / hydroxylamine hydrochloride; pyridine / 0.5 h / Heating 2: hydrazine hydrate; acetic acid / Heating 3: 78 percent / phosphorus oxychloride; pyridine / 1 h / 110 °C 4: 68 percent / hydrazine hydrate / ethanol / 1 h / Heating 5: 82 percent / 12 h / 45 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / 98percent N2H4*H2O / ethanol / 1 h / Heating 2: 1) KOH / 1) MeOH, 15-20 min, reflux, 2) 1.0 h, reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / 98percent N2H4*H2O / ethanol / 1 h / Heating 2: 1) KOH / 1) MeOH, 15-20 min, reflux, 2) 1.0 h, reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 2: 2) Na/CH3OH / 1) CH2Cl2, 4 h, reflux 2) 2 h, reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / CH2Cl2 2: 2) Na/CH3OH / 1) CH2Cl2, 4 h, reflux 2) 2 h, reflux 3: 56 percent / KOH / propan-2-ol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi, N,N,N',N'-tetramethylethylenediamine / 1.) THF, a) -78 deg C, 0.5 h, b) -23 deg C, 0.5 h, 2.) a) -78 deg C, 2 h, b) 20 deg C, 3 h 2: 95 percent / 50 percent sulphuric acid / 0.75 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi, N,N,N',N'-tetramethylethylenediamine / 1.) THF, a) -78 deg C, 0.5 h, b) -23 deg C, 0.5 h, 2.) a) -78 deg C, 2 h, b) 20 deg C, 3 h 2: 95 percent / 50 percent sulphuric acid / 0.75 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium/charcoal; ethyl cinnamate 2: KMnO4; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: platinum; aq.-ethanolic hydrochloric acid / Hydrogenation 2: palladium/charcoal; ethyl cinnamate 3: KMnO4; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid anhydride / 150 °C 2: aluminium chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methanol; 3-benzoylpyridine-2-carboxylic acid With sulfuric acid In methanol at 20℃; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water | 71 Production Example 71 Manufacture of 3-phenylmethyl-6-(4H-[1,2,4]triazole-3- yl-sulfanyl)-N-(thiazole-2-yl)-2-pyridine carboxamide 3-benzoyl-2-pyridinecarboxylic acid (2.0 g; 8.8 mmol) was dissolved in 10 ml of methanol and 10 drops of concentrated sulfuric acid were dropped thereinto at room temperature followed by heating to reflux for a whole day and night. After cooling, methanol was evaporated therefrom followed by neutralizing with a saturated aqueous solution of sodium hydrogen carbonate. Extraction with chloroform was conducted followed by drying over sodium sulfate and concentrating to give 2.0 g of a crude product of 3-benzoyl- 2-pyridinecarboxylate methyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | With thionyl chloride; acetic anhydride In tetrahydrofuran; N,N-dimethyl acetamide; water; toluene; acetonitrile | 205.1 2-(Aminomethyl)-4-isobutyl-5-phenyl[1,7]naphthyridin-8(7H)-one dihydrochloride (1) To a suspension of 3-benzoylpyridin-2-carboxylic acid (2.27 g, 10 mmol) in toluene (20 ml) was added thionyl chloride (0.88 ml, 12 mmol) and the mixture was stirred at 100° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (20 ml). The obtained solution was added dropwise to (isobutylamino)-acetonitrile (1.68 g, 15 mmol) in N,N-dimethylacetamide (20 ml) and the mixture was stirred at 70° C. for 12 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To a solution of the residue and acetic anhydride (1.1 ml, 12 mmol) in acetonitrile (6.0 ml, 40 mmol) at 0° C. and the mixture was stirred at room temperature for 15 h. Water was added to the reaction mixture and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration. The obtained crystals were recrystallized from tetrahydrofuran-diisopropyl ether to give 7-isobutyl-8-oxo-5-phenyl-7,8-dihydro[1,7]naphthyridine-6-carbonitrile (2.65 g, 87.5%) as crystals. Melting point 221-222° C. Elemental analysis for C19H17N3O Calculated: C, 75.23; H, 5.65; N, 13.85. Found: C, 75.20; H, 5.72; N, 13.85. 1H-NMR(CDCl3) δ: 1.06 (6H, d, J=7.0 Hz), 2.30-2.51 (1H, m), 4.24 (2H, d, J=7.8 Hz), 7.37-7.46 (2H, m), 7.52-7.61 (4H, m), 7.72 (1H, dd, J=1.8, 8.3 Hz), 9.01 (1H, dd, J=1.8, 8.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 3-benzoylpyridine-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; Inert atmosphere; Stage #2: anthranilic acid amide In dichloromethane at 20℃; | 1.B 3-Benzoyl-Pyridine-2-Carboxylic Acid (2-Carbamoyl-Phenyl)-Amide (Intermediate Compound) 1-Hydroxybenzoetriazole (25 mg, 0.18 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, hydrochloride (520 mg, 2.7 mmol) and triethylamine (360 mg, 3.6 mmol) were added to a solution of 3-benzoyl-pyridine-2-carbonylic acid (500 mg, 2 mmol) in dichloromethane (50 mL) under a nitrogen atmosphere at 0° C. After stirring for 30 minutes at 0° C. anthranilamide (250 mg, 1.8 mmol) was added and stirring was continued at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate (250 mL), washed with brine, dried over anhydrous sodium sulphate, filtered and evaporated. The crude product was purified by column chromatography to give 3-benzoyl-pyridine-2-carboxylic acid (2-carbamoyl-phenyl)-amide (50 mg, 0.14 mmol, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With hydrazine In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: hydrazine hydrate / ethanol / 80 °C 2.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h 2.2: 4 h 3.1: pyridine / dichloromethane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate In ethanol at 80℃; | g.7.7A Example 7A5-phenylpyrido[2,3-d]pyridazin-8-olA mixture of 3-benzoylpicolinic acid (0.272 g, 0.120 mmol) and hydrazine hydrate (0.17 mL, 0.37 mmol) in EtOH (3.3 mL) was stirred at 80° C. overnight, concentrated, diluted with saturated aqueous NaHCO3, extracted with CH2Cl2, dried (Na2SO4), and concentrated to give the title compound as a white solid (0.28 g, 0.12 mmol). 1H NMR (300 MHz, DMSO-d6) δ 13.09 (s, 1H), 9.10 (dd, 1H), 8.09 (dd, 1H), 7.88 (dd, 1H), 7.54-7.63 (m, 5H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / ethanol / 80 °C 2.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h 2.2: 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C33H49N4O10Pol With tetrakis(triphenylphosphine) palladium(0); phenylsilane In dichloromethane Stage #2: 3-benzoylpyridine-2-carboxylic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C32H47N4O10PolS With tetrakis(triphenylphosphine) palladium(0); phenylsilane In dichloromethane Stage #2: 3-benzoylpyridine-2-carboxylic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In toluene for 2h; Dean-Stark; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 2 h / Dean-Stark; Inert atmosphere; Reflux 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
108 mg | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; | General Procedure for the Preparation of the 1,2,4-Triazoles. General procedure: Removal of the Boc protecting group of compound 5 was preformed at room temperature for 1 h with a solution of HCl 4N in dioxane. The mixture was then concentrated in vacuo, diluted with MeOH, and concentrated several times in vacuo. The residue was coupled with various carboxylic acids (1.1 equiv), in the presence of BOP (1.1 equiv) and DIEA (pH=9) for 2 h, in DCM. The mixture was then concentrated in vacuo, and the residue was dissolved in AcOEt. The organic layer was successively washed with aqueous solutions of 1M KHSO4, saturated NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to yield the desired compound. All the final compounds were purified by preparative HPLC on a C18 column using a water/acetonitrile/TFA 0.1% gradient. |