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CAS No. : | 3238-55-9 | MDL No. : | MFCD00023486 |
Formula : | C8H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZHAZHKPVEROFLH-UHFFFAOYSA-N |
M.W : | 135.16 | Pubchem ID : | 520574 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
97% | With diethyl ether at -20 - 20℃; for 4h; | |
85% | In diethyl ether for 1h; Heating; | |
85% | Stage #1: 2-Cyanopyridine; ethylmagnesium bromide In diethyl ether at -15 - 20℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water at 20℃; for 0.25h; Inert atmosphere; |
82% | Stage #1: 2-Cyanopyridine; ethylmagnesium bromide In tetrahydrofuran; diethyl ether at -15 - 20℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethylene glycol at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; | |
76% | Stage #1: 2-Cyanopyridine; ethylmagnesium bromide In diethyl ether at -15 - 20℃; for 3h; Stage #2: With hydrogenchloride; water In diethyl ether at 20℃; for 0.25h; | |
57% | In methanol; diethyl ether; water at -20℃; | |
With diethyl ether anschliessenden Behandeln des Reaktionsgemisches mit wss.Ammoniumchlorid-Loesung; | ||
Stage #1: 2-Cyanopyridine; ethylmagnesium bromide Stage #2: With water Further stages.; | ||
Stage #1: 2-Cyanopyridine; ethylmagnesium bromide Inert atmosphere; Stage #2: With water | ||
Stage #1: 2-Cyanopyridine; ethylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Stage #2: With water; citric acid In tetrahydrofuran; diethyl ether | Intermediate of Formula XXIV; 1-Pyridin-2-yl-propan-1-one; 3M Et2O solution of ethylmagnesium bromide (19.2 mL, 57.6 mmol) was added to a stirred solution of pyridine-2-carbonitrile (5.0 g, 48.0 mmol) in THF (80 mL) at -78° C. The reaction mixture was allowed to warm to rt. The reaction mixture was acidified with aqueous citric acid solution. THF was removed in vacuo and the product was extracted with EtOAc. The organic layers were combined and washed with aqueous NaHCO3 and brine. Upon concentration in vacuo, the product was obtained as a pale yellow colored liquid. ESMS m/e: 271 (2M+H)+. | |
Stage #1: 2-Cyanopyridine; ethylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Stage #2: With water; citric acid In tetrahydrofuran; diethyl ether Stage #3: With sodium hydrogencarbonate In diethyl ether; water; ethyl acetate | XXIV 3M Et2O solution of ethylmagnesium bromide (19.2 ml_, 57.6 mmol) was added to a stirred solution of pyridine-2-carbonitrile (5.0 g, 48.0 mmol ) in THF (80 ml_) at -78 0C. The reaction mixture was allowed to warm to rt. The reaction mixture was acidified with aqueous citric acid solution. THF was removed in vacuo and the product was extracted with EtOAc. The organic layers were combined and washed with aqueous NaHCO3 and brine. Upon concentration in vacuo, the product was obtained as a pale yellow colored liquid. ESMS m/e: 271 (2M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 25℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In benzene | ||
With toluene-4-sulfonic acid | ||
With toluene-4-sulfonic acid In toluene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With calcium sulfate In benzene for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In <i>tert</i>-butyl alcohol; benzene for 5h; Irradiation; other solv.; | |
81% | In <i>tert</i>-butyl alcohol; benzene for 5h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium(II) perchlorate; N-<α-methylbenzyl>-1-propyl-2,4-dimethyl-1,4-dihydronicotinamide In acetonitrile at 25℃; Yield given. Title compound not separated from byproducts; | ||
With formic acid; RuCl(p-cymene)[N-(p-tosyl)-(1R,2R)-diphenylethylenediamine]; triethylamine at 27℃; for 24h; Title compound not separated from byproducts; | ||
With Pseudomonas putida UV4 Enzymatic reaction; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; | |
With 3-chloro-benzenecarboperoxoic acid In chloroform a) RT, 0.5 h, b) reflux, 0.5 h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With pyridine; N-hydroxyphthalimide; tetrabutylammonium tetrafluoroborate; oxygen In 2,2,2-trifluoroethanol; acetonitrile at 35℃; Electrolysis; | 2.2.1 Procedure for mono-oxidation General procedure: An undivided cell was equipped with a magnet stirrer, platinum plate electrode (1.0×1.0×0.3 cm3), as the working electrode and counter electrode. Substrate (0.5 mmol),nBu4NBF4 (0.5 mmol, 164.6 mg), N-hydroxyphthalimide (NHPI, 0.1 mmol, 16.3 mg), and pyridine (1.0 mmol, 82 μL)were added to MeCN/2,2,2-trifluoroethan-1-ol (TFE) (5:1,3 mL). The electrolysis was conducted in an undivided cell equipped with O2 balloon at a constant current of 5 mA at room temperature (25-30 °C). When the reaction was completed, the solvent was removed under reduced pressure and the remaining crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate(PE/EA)=30:1-10:1) to afford the corresponding aromatic ketone product. |
60% | With N-hydroxyphthalimide; oxygen; 2,6-dimethylpyridine perchlorate In acetonitrile at 20℃; for 12h; Electrolysis; | |
15% | With tert.-butylhydroperoxide; ZnCrCO3-HTlc In <i>tert</i>-butyl alcohol for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium hydroxide; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2-bromo-pyridine; tributyl(1-ethoxyprop-1-enyl)stannane With copper(l) iodide In acetonitrile Heating; Stage #2: With hydrogenchloride In acetonitrile for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 15% 2: 40% | Stage #1: 1-(pyridin-2-yl)-prop-2-en-1-ol With sodium hydride In toluene at 20℃; for 3h; Stage #2: 2-Chloro-3-nitropyridine In toluene at 70℃; for 144h; | |
1: 26% 2: 29% | In toluene at 70℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In chloroform at 110℃; for 48h; | |
85% | In chloroform at 110℃; for 48h; | |
84% | With 1,10-Phenanthroline; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; |
76% | With sodium hydride In tetrahydrofuran at 0 - 20℃; for 9h; Inert atmosphere; | 4.3. Conversion of allylic alcohols to saturated ketones General procedure: To a round-bottom flask that was flame-dried and cooled under nitrogen were added allylic alcohol 51 (0.5 mmol) and THF (2.5 mL). After stirring at 0 °C for 5 min, NaH powder (1 mmol, 2 equiv) was added in one portion, the mixture was then allowed to warm to room temperature. The reaction was quenched by addition of saturated NH4Cl (2 mL) after the indicated time, extracted with EtOAc (10 mL×2), and washed by brine (15 mL). The combined organic phase was dried over MgSO4, the solvent was removed under vacuum, and the residue was purified by flash chromatography on silica gel to give the desired ketone product 52. |
28 %Spectr. | With Milstein's PNN catalyst In (2)H8-toluene for 24h; Reflux; Inert atmosphere; | |
1.13 g | With 1,10-Phenanthroline; sodium t-butanolate In toluene at 100℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With hydrogen In ethanol at 22℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: 2-propionylpyridine With N,N,N,N,-tetramethylethylenediamine; sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.08333h; Inert atmosphere; Stage #2: Allyl chloroformate In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; optical yield given as %de; | |
59% | Stage #1: 2-propionylpyridine With N,N,N,N,-tetramethylethylenediamine; sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: Allyl chloroformate In tetrahydrofuran at -78℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With acetic acid In methanol at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 2-Cyanopyridine; ethylmagnesium halide In diethyl ether at -15 - 20℃; for 4h; Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogen bromide; bromine; acetic acid at 20℃; for 2h; | 2-Bromo-1-pyridin-2-yl-propan-1-one; 33% Hydrogen bromide in acetic acid was added (7.8 mL, 45.1 mmol) to a solution of 1-pyridin-2-yl-propan-1-one (6.0 g, 45.1 mmol) in acetic acid (50 mL) with vigorous stirring. Bromine (2.32 mL, 45.1 mmol) was added to the solution and the reaction was stirred at rt for 2 h. The orange colored solution was concentrated in vacuo to give the desired compound (15.7 g, >99) as a semi solid. ESMS m/e: 213 (M+H)+. |
99% | With hydrogen bromide; bromine In acetic acid at 20℃; for 2h; | XXII 2-Bromo-1-pyridin-2-yl-propan-1-one: 33 % Hydrogen bromide in acetic acid was added (7.8 mL, 45.1 mmol) to a solution of 1-pyridin-2-yl-propan-1-one (6.0 g, 45.1 mmol) in acetic acid (50 mL) with vigorous stirring. Bromine (2.32 mL, 45.1 mmol) was added to the solution and the reaction was stirred at rt for 2 h. The orange colored solution was concentrated in vacuo to give the desired compound (15.7 g, >99) as a semi solid. ESMS m/e: 213 (M+H)+. |
90% | With aluminium trichloride; bromine In diethyl ether for 6h; |
With bromine In tetrachloromethane for 1h; Reflux; | ||
With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrile at 60℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 90 percent / Br2; AlCl3 / diethyl ether / 6 h 2: 100 percent / tetrahydrofuran / 14 h / 20 °C 3: 70 percent / aq. NaOH / diethyl ether / 2.5 h 4: 96 percent / K2CO3 / acetonitrile / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 90 percent / Br2; AlCl3 / diethyl ether / 6 h 2.1: 100 percent / tetrahydrofuran / 14 h / 20 °C 3.1: 70 percent / aq. NaOH / diethyl ether / 2.5 h 4.1: 96 percent / K2CO3 / acetonitrile / 72 h / 20 °C 5.1: mCPBA / CH2Cl2 / 5 h / -78 °C 5.2: 71 percent / NH4OAc; AcOH / 18 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / Br2; AlCl3 / diethyl ether / 6 h 2: 100 percent / tetrahydrofuran / 14 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 90 percent / Br2; AlCl3 / diethyl ether / 6 h 2: 100 percent / tetrahydrofuran / 14 h / 20 °C 3: 70 percent / aq. NaOH / diethyl ether / 2.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane; TMEDA / tetrahydrofuran / 1 h / -78 °C 1.2: 59 percent / tetrahydrofuran / 0.08 h / -78 °C 2.1: Pd2(dba)3*CHCl3; (R,R)-1',2'-bis(o-C6H4(PPh2)CONH)-9,10-ethanoantracene / dioxane / 1 h / 23 °C 3.1: aq. sodium periodate; OsO4 / ethyl acetate / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hexamethyldisilazane; TMEDA / tetrahydrofuran / 1 h / -78 °C 1.2: 59 percent / tetrahydrofuran / 0.08 h / -78 °C 2.1: Pd2(dba)3*CHCl3; (R,R)-1',2'-bis(o-C6H4(PPh2)CONH)-9,10-ethanoantracene / dioxane / 1 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hexamethyldisilazane; TMEDA / tetrahydrofuran / 1 h / -78 °C 1.2: 59 percent / tetrahydrofuran / 0.08 h / -78 °C 2.1: Pd2(dba)3*CHCl3; (R,R)-1',2'-bis(o-C6H4(PPh2)CONH)-9,10-ethanoantracene / dioxane / 1 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 60 percent / H2 / Rh/alumina / ethanol / 48 h / 22 °C 2: 56 percent Chromat. / Ag2CO3/Celite / benzene / 11 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 60 percent / H2 / Rh/alumina / ethanol / 48 h / 22 °C 2: 40 percent Chromat. / Ag2CO3/Celite / benzene / 11 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: p-toluenesulfonic acid / toluene / 2 h / Heating 2: 98 percent / H2 / Rh/alumina / ethanol / 90 h / 22 °C 3: 95 percent / aq. HCl / acetone / 15 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / toluene / 2 h / Heating 2: 98 percent / H2 / Rh/alumina / ethanol / 90 h / 22 °C | ||
Multi-step reaction with 2 steps 1: TsOH / benzene 2: H2 / PtO2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl / tetrahydrofuran 2: H2 / Pd/C / methanol / 18 h / 2068.59 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl / tetrahydrofuran 2: H2 / Pd/C / methanol / 18 h / 2068.59 Torr 3: CMC; DMAP / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: HCl / tetrahydrofuran 2: H2 / Pd/C / methanol / 18 h / 2068.59 Torr 3: CMC; DMAP / tetrahydrofuran 4: tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / PtO2 / acetic acid 2: 1) Na2CO3, 2) n-BuLi |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: CaSO4 / benzene / 24 h / Heating 2: NaBH4 / methanol / 12 h / 50 °C 3: BBr3 / CH2Cl2 / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: CaSO4 / benzene / 24 h / Heating 2: NaBH4 / methanol / 12 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; acetic acid | 2 1-(2-Pyridyl)-1-propanone-1-(1,3-benzoxazol-2-yl)-hydrazone (1a-13) EXAMPLE 2 1-(2-Pyridyl)-1-propanone-1-(1,3-benzoxazol-2-yl)-hydrazone (1a-13) A mixture of 2-propionyl pyridine (0.60 g, 4.42 mmol) and 2-hydrazinobenzoxazole (0.60 g 4.02 mmol) in 25 ml of methanol is refluxed for 24 hours after the addition of 6 drops of glacial acetic acid. The reaction mixture is stored over night in the refrigerator at approximately 5° C. The precipitate is filtered and recrystallized from diisopropyl ether. Yield: 0.68 g (64% of theory). C15H14N4O (266.31) 1H-NMR (δ, ppm) 1.08 (t, 3H), 3.05 (q, 2H), 7.05-7.46 (m, 4H), 7.37 (qd, 1H), 7.84 (ddd, 1H), 8.22 (br.s 1H), 8.60 (qd, 1H), 11.48 (br.s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; manganese dioxide; acetic anhydride In methanol; dichloromethane; water; acetic acid | 19 Preparation of ethyl-2-pyridylketone-1'-phthalazinylhydrazine (PH 22-25) 19 g of 2-propylpyridine-N-oxide were dissolved in 40 ml of glacial acetic acid/40 ml of acetic anhydride and stirred for 6 hours at 85° C. and 12 hours at ambient temperature. Excess anhydride was decomposed with H2 O, the solution was neutralized with Na2 CO3 and extracted with diethyl ether. After rotating in the ether phase, 12 g of 2-(1-acetoxypropyl)-pyridine remained. This product was dissolved in 120 ml of methanol (70%), mixed with 4 g of NaOH and refluxed for 6 hours. After rotating out the methanol mixing took place with water, extraction with diethyl ether and the organic phase was rotated in. 5.4 g of 2-(1-hydroxypropyl)-pyridine were left. 0.5 g of this substance was refluxed for 2 hours with 1 g of MnO2 and 30 ml of dichloromethane. After filtering off the MnO2, rotation in took place to dryness. 0.3 g of ethyl-2-pyridylketone was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | In toluene at 110℃; for 18h; | |
31% | In toluene at 110℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 50% 2: 7% | In toluene at 70℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With n-butyllithium In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | |
60% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-propionylpyridine In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In ethyl acetate at 20 - 75℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Stage #1: 2-propionylpyridine With bromine In tetrachloromethane for 1h; Reflux; Stage #2: 2-Amino-2-methyl-1-propanol In acetonitrile for 24h; | Synthesis of 3,5,5-Trimethyl-2-(pyridin-2-yl)morpholin-2-ol (6).; l-(Pyridin-2-yl)propan-l-one (8n, 1.71 g, 0.013 mol) was dissolved in CC14 (50 mL). Bromine(0.66 mL, 12.7 mmol) was added and gently refluxed for 1 h. The solvent was decanted. The orange solid at the bottom of flask was washed with ether, vacuum dried, and then suspend in CH3CN (40 mL), followed by the addition of 2-amino-2-methyl-l-propanol (2.30 g, 0.0254 mol). The reaction mixture was stirred for 24 h. The precipitate was separated by filtration and was extracted with EtOAc. The organic layer was washed with aqueous NaHC(¾ and dried (Na2SC>4) and concentrated to give a orange oil. The residue was purified by column chromatography on silica gel using, CH2Cl2-MeOH (50: 1 to 20: 1) with 1% NH4OH) to give 0.94 g (33%) of free base that was converted to the corresponding tartrate salt: ¾ MR (CDC13) δ 8.55-8.51 (m, 1H), 7.84-7.59 (m, 1H), 7.63- 7.57 (m, 1H), 7.34-7.26 (m, 1H), 6.00 (s, 1H), 3.97-3.91 (m, 1H), 3.47-3.37 (m, 2H), 1.42 (s, 3H), 1.10 (s, 3H), 0.74 (d, 3H, J = 6.5 Hz); 13C NMR (CDC13) δ 158.6, 147.2, 137.5, 123.6, 120.5, 94.2, 70.0, 52.1, 48.9, 27.1, 22.9, 16.2; LCMS (ESI) m/z 223 A [(M - tartrate)+, M = Ci6H24N208]; Anal. (Ci6H24N2Cr0.5H2O) calcd: C 50.39, H 6.61, N 7.35; found: C 50.44, H 6.80, N 7.09. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: propionaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Stage #3: With iodine; potassium carbonate In <i>tert</i>-butyl alcohol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | Stage #1: 2-propionylpyridine With titanium(IV) isopropylate; (S)-3,3'-bis(4-phenyl-1H-1,2,3-triazol-1-yl)-[1,1'-binaphthalene]-2,2'-diol In toluene at 20 - 25℃; for 0.5h; Inert atmosphere; Stage #2: diethylzinc In toluene at 20 - 25℃; for 19h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: ethyl bromide With iodine; magnesium In tetrahydrofuran Stage #2: 2-Cyanopyridine In tetrahydrofuran at 0℃; | |
Stage #1: ethyl bromide With magnesium In diethyl ether Reflux; Stage #2: 2-Cyanopyridine In diethyl ether at -0.16℃; Reflux; Stage #3: With sulfuric acid; water In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 23% 2: 14% | With trimethylsilyl trifluoromethanesulfonate In water; acetonitrile at 0℃; for 12h; Reflux; Overall yield = 37 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol; water at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol; water at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With C60H60P2Rh(1+)*BF4(1-); hydrogen In dichloromethane at 20℃; for 24h; Autoclave; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With 2,6-dimethylpyridine; C38H38IrN4S2(1+)*F6P(1-) In methanol; acetonitrile at 40℃; for 36h; Schlenk technique; Inert atmosphere; Irradiation; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1.25 h / 5 - 20 °C 2: sodium t-butanolate; 1,10-Phenanthroline / toluene / 1 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C 2: 1,10-Phenanthroline; sodium t-butanolate / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 2,6-dimethylpyridine; 2C51H36IrN9*6C2H3N*2H2O*3Co(2+)*6ClO4(1-) In methanol; acetonitrile at 40℃; for 36h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
104 mg | With iodine In ethanol at 70℃; Inert atmosphere; | 1 5-methyl-4-(2-pyridyl)thiazol-2-amine To a 40 mL vial was added 1-Pyridin-2-yl-propan-1-one (100 mg, 0.74 mmol),thiourea (112 mg, 1.48 mmol), and anhydrous ethanol (1 mL) followed by iodine (188mg, 0.74 mmol). The mixture was heated at 70 °C under nitrogen overnight. Thereaction mixture was cooled to room temperature and diluted with EtOAc. Theorganic layer was washed with saturated aqueous sodium thiosulfate solution andsaturated NaHCO3. The organic layer was then washed with 1 N HC1. The aqueouslayer was basified with saturated aqueous sodium bicarbonate to pH = 8 and extracted with EtOAc. The combined organic layer was dried over Na2504, filtered andconcentrated to obtain a tan solid (104 mg), which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With [2,2]bipyridinyl; TEMPOL; copper diacetate; sodium acetate In 1,2-dichloro-benzene at 140℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 4 h / 60 °C 2: potassium carbonate / acetonitrile / 20 °C 3: bis(1,5-cyclooctadiene)diiridium(I) dichloride; f-amphox; caesium carbonate; hydrogen / isopropyl alcohol / 12 h / 20 - 30 °C / 15201 Torr / Inert atmosphere; Autoclave |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 4 h / 60 °C 2: potassium carbonate / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70 mg | With acetic acid In water at 50℃; for 2h; | 5 Synthesis of compound B; 2-[ (lE)-l-(2-{6-methyl-5H-[ 1, 2, 4 ]triazino[5, 6-b ]indole-3-yl}hydrazin-l- ylidene)propyl]pyridine l-(pyridin-2-yl)propan-l-one (35 mg, 0.26 mmol) was dissolved in a water -acetic acid mixture (20:1, 10 mL) then 3-hydrazinyl-6-methyl-5H-[l,2,4]triazino[5,6-b]indole (50 mg, 0.23 mmol) was added. The reaction mixture was stirred for 2 hours at 50°C. After evaporating the solvents, a dark green solid was obtained (70 mg). LC shows pure product with an isomer ratio of 95:5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With cobalt(II) 5,10,15,20-tetraphenylporphyrin; caesium carbonate; toluene-4-sulfonic acid hydrazide In benzene at 100℃; for 12h; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With iodine; sodium acetate In 1,2-dichloro-ethane for 2.5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; zinc(II) acetylacetonate; benzoic acid In 1,2-dichloro-ethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With C49H45N5O4S2; nickel diacetate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20℃; for 42h; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85 % ee | With nickel(II) fluoride tetrahydrate; [3aS-[2(3'aRS,8'aSR),3aα,8aα]]-2,2'-(2,6-pyridinediyl)bis-[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] In tetrahydrofuran at 10℃; for 48h; Schlenk technique; Molecular sieve; Inert atmosphere; Overall yield = 75 percent; Overall yield = 31.4 mg; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
800 mg | Stage #1: 2-propionylpyridine With potassium carbonate In water for 0.5h; Stage #2: Glyoxilic acid In water Stage #3: With hydrazine hydrate; acetic acid In water for 144h; | 1 Step 1. A flask was charged with potassium carbonate (8.8 mmol). The solid was dissolved in water, then l-(pyridin-2-yl)propan-l-one (4.4 mmol) was added at once. The solution was stirred for 30 minutes, and then glyoxylic acid was added at once (4.4 mmol). After stirring overnight, the reaction was acidified with acetic acid (17.6 mmol), then hydrazine monohydrate was added in one portion (8.8 mmol). The reaction was stirred for 6 days, with an additional 2 mL of acetic acid added every 2 days. The reaction was partially concentrated under reduced pressure, then extracted with 20% isopropanol in dichloromethane, dried over anhydrous sodium sulfate, then concentrated under reduced pressure to give 5-methyl-6-(pyridin-2-yl)pyridazin-3(2H)-one as a solid (800 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With acetic acid In methanol for 2h; Reflux; | 4.4. General procedure for the synthesis of target compounds (4a-s,5a-u) General procedure: The detailed information on the characterization of compounds2, 4a 4o, 4r and 4s were reported in our published article [26,36].In a 25mL round-bottom flask, the intermediate compounds 3ag(1 mmol) was dissolved in methanol (5 mL), following by addingappropriate aldehyde or ketone (1.1 mmol) and a catalytic amountof AcOH (0.01 mmol) in turn. The system was heated under refluxfor 2 h, subsequently cooled to room temperature, the precipitationwas filtered and recrystallized with methanol to get target compounds4a-s and 5a-u in 65e85% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In 1,2-dichloro-benzene at 120℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With palladium diacetate; caesium carbonate In 1,3,5-trimethyl-benzene at 120℃; for 14h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: methanol; 2-propionylpyridine With [pentamethylcyclopentadienyl*Ir(2,2′-bpyO)(OH)][Na]; caesium carbonate at 120℃; for 12h; Schlenk technique; Stage #2: With water at 120℃; for 12h; Schlenk technique; | 4.1. General synthesis of b-methylated secondary alcohols usingmethanol General procedure: In air, in a 25mL Schlenk tube were added ketone (1 mmol), cat. 9(5.5 mg, 1 mol%), Cs2CO3 (97.8 mg, 0.3 equiv), and MeOH (2 mL). Thereaction mixture was heated at 120 C in an oil bath for 12 h underairtight conditions. After cooling to ambient temperature, 2mL H2Owas added, and the mixture was heated at 120 C for another 12 h.After the given reaction time, the mixture was then cooled to ambienttemperature, concentrated under reduced pressure, and purifiedby flash column chromatography with hexanes/ethyl acetate(50/1-100/1, v/v) to afford the target product, which was identified by NMR analyses. All analytical data of the known compounds areconsistent with those reported in the literature. Some unknowncompounds are detected by NMR and HRMS analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99 % ee | With glucose dehydrogenase; ammonium hydroxide; galactose; amine dehydrogenase from Jeotgalicoccus aerolatus K67S/N260L/E113V/V291G mutant; ammonia hydrochloride In dimethyl sulfoxide at 30℃; for 48h; Enzymatic reaction; enantioselective reaction; |
Tags: 3238-55-9 synthesis path| 3238-55-9 SDS| 3238-55-9 COA| 3238-55-9 purity| 3238-55-9 application| 3238-55-9 NMR| 3238-55-9 COA| 3238-55-9 structure
[ 165126-71-6 ]
1-(6-Methylpyridin-2-yl)propan-1-one
Similarity: 0.98
[ 165126-71-6 ]
1-(6-Methylpyridin-2-yl)propan-1-one
Similarity: 0.98
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