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CAS No. : | 583-05-1 | MDL No. : | MFCD00092889 |
Formula : | C11H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RBLXWIPBPPVLPU-UHFFFAOYSA-N |
M.W : | 176.21 | Pubchem ID : | 136371 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
With sodium cyanide In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With acetic acid In methanol at 50℃; | |
84% | With acetic acid In methanol at 50℃; for 12h; | |
84% | With acetic acid In methanol at 50℃; for 12h; |
75% | With acetic acid In methanol at 50℃; for 1h; | |
70% | With acetic acid In methanol | |
70% | With acetic acid In methanol | |
With acetic acid In methanol at 50℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 84 percent / acetic acid / methanol / 12 h / 50 °C 2: 91 percent / CH2Cl2 / 13 h / 23 °C | ||
Multi-step reaction with 2 steps 1: 84 percent / acetic acid / methanol / 12 h / 50 °C 2: 1.22 g / CH2Cl2 / 13 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: tert-Butyl 2-aminopropanoate hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 1-phenylpentane-1,4-dione With iodine In tetrahydrofuran at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With indium; acetic acid In toluene for 2h; Inert atmosphere; Reflux; | 37 4.2.37. 1-(3-Fluorophenyl)-2-methyl-5-phenyl-1H-pyrrole (39) General procedure: Nitrobenzene derivative (1.0mmol) was added to a mixture of indium powder (460mg, 4.0mmol), and acetic acid (0.572mL, 10mmol) in toluene (2mL), followed by the addition of 2,5-hexadione or 1-phenyl-1,4-pentanedione (1.0mmol) in toluene (3mL). The reaction mixture was stirred at 80°C for 2,5-hexadione (or reflux for 1-phenyl-1,4-pentadione) under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30mL), filtered through Celite, poured into 10% NaHCO3 (30mL), and then extracted with ethyl acetate (30mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with hexane for most derivatives or ethyl acetate/hexane (v/v=5:95) for benzonitrile derivatives through a neutral silica gel column to give the corresponding pyrroles. The structures of the pyrroles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. If it is an unknown compound, elemental analysis data were reported additionally. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With indium; acetic acid In toluene for 24h; Inert atmosphere; Reflux; | 41 4.2.41. 2-(2-Methyl-5-phenyl-1H-pyrrol-1-yl)benzonitrile (43) General procedure: Nitrobenzene derivative (1.0mmol) was added to a mixture of indium powder (460mg, 4.0mmol), and acetic acid (0.572mL, 10mmol) in toluene (2mL), followed by the addition of 2,5-hexadione or 1-phenyl-1,4-pentanedione (1.0mmol) in toluene (3mL). The reaction mixture was stirred at 80°C for 2,5-hexadione (or reflux for 1-phenyl-1,4-pentadione) under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30mL), filtered through Celite, poured into 10% NaHCO3 (30mL), and then extracted with ethyl acetate (30mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with hexane for most derivatives or ethyl acetate/hexane (v/v=5:95) for benzonitrile derivatives through a neutral silica gel column to give the corresponding pyrroles. The structures of the pyrroles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. If it is an unknown compound, elemental analysis data were reported additionally. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aminosulfonic acid In water at 60℃; for 5h; | Synthesis of 2-methyl-1,5-diphenyl-1H-pyrrole (4); Typical Procedure General procedure: Cu(OTf)2 (5 mol%), MnCl2*4H2O (5 mol%), DBU (1.5 equiv.) and aqueous TBHP (4 equiv., 70% in water) were sequentially added to a mixture of styrene (0.5 mmol, 1 equiv.) and acetone (3 mL). The reaction was heated at 60 °C for 20 h, then cooled to room temperature before aniline (0.5 mmol, 1 equiv.) and H2NSO3H (5 mol%) was added and the reaction mixture heated at 60 °C for 5 h. The organic phase was removed under reduced pressure and the crude product purified by silica gel column chromatography (EtOAc-hexanes, 20%) to afford 4a as a pale-yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With indium; acetic acid In toluene for 8h; Inert atmosphere; Reflux; | 2. General procedure for the indium-mediated reductive reaction of 2,6-disubstutited nitroanilines with 2,5-hexanedione or 1-phenyl-1,4-pentanedione to obtain 4-(1H-pyrrol-1-yl)aniline derivatives General procedure: To a mixture of the 2,6-dihalo-4-nitroaniline derivative (1.0 mmol) and indium powder (459 mg, 4.0 mmol) in toluene (2.5 mL) was added acetic acid (573 μL, 10 mmol) followed by the 1,4-diketone (2.0 mmol) in toluene (2.5 mL). The resulting mixture was stirred at 80 qC (2,5-hexanedione) or reflux (1-phenyl-1,4-pentanedione) under a nitrogen atmosphere. After the reaction was complete, the reaction mixture was diluted with EtOAc (30 mL) or CH 2 Cl 2 (30 mL) and filtered through a celite pad. The filtrate was poured onto a 10% aqueous solution of NaHCO 3 (30 mL), the layers separated, and the aqueous layer extracted with EtOAc (30 mL u 3) or CH2Cl2 (30 mL u 3). The combined organic layers were dried over MgSO 4 , filtered, and concentrated in vacuo. The resulting residue was purified using flash column chromatography on neutral silica gel eluted with EtOAc/hexane (v/v = 5/95) to give the corresponding pyrrole product. The structures of the pyrrole products, which were mostly novel compounds, were characterized using 1 H NMR, 13 C NMR and FTIR spectroscopy, GC-MS, and HRMS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 82% 2: 11% | With indium; acetic acid In toluene for 12h; Inert atmosphere; Reflux; | 2. General procedure for the indium-mediated reductive reaction of 2,6-disubstutited nitroanilines with 2,5-hexanedione or 1-phenyl-1,4-pentanedione to obtain 4-(1H-pyrrol-1-yl)aniline derivatives General procedure: To a mixture of the 2,6-dihalo-4-nitroaniline derivative (1.0 mmol) and indium powder (459 mg, 4.0 mmol) in toluene (2.5 mL) was added acetic acid (573 μL, 10 mmol) followed by the 1,4-diketone (2.0 mmol) in toluene (2.5 mL). The resulting mixture was stirred at 80 qC (2,5-hexanedione) or reflux (1-phenyl-1,4-pentanedione) under a nitrogen atmosphere. After the reaction was complete, the reaction mixture was diluted with EtOAc (30 mL) or CH 2 Cl 2 (30 mL) and filtered through a celite pad. The filtrate was poured onto a 10% aqueous solution of NaHCO 3 (30 mL), the layers separated, and the aqueous layer extracted with EtOAc (30 mL u 3) or CH2Cl2 (30 mL u 3). The combined organic layers were dried over MgSO 4 , filtered, and concentrated in vacuo. The resulting residue was purified using flash column chromatography on neutral silica gel eluted with EtOAc/hexane (v/v = 5/95) to give the corresponding pyrrole product. The structures of the pyrrole products, which were mostly novel compounds, were characterized using 1 H NMR, 13 C NMR and FTIR spectroscopy, GC-MS, and HRMS. |