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CAS No. : | 18159-22-3 | MDL No. : | MFCD00894448 |
Formula : | C12H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OGGDCEFWAMGBOB-UHFFFAOYSA-N |
M.W : | 201.22 | Pubchem ID : | 14985839 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 diphenyl phosphoryl azide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 2: 84 percent / n-BuLi / tetrahydrofuran / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 2: 84 percent / n-BuLi / tetrahydrofuran / 3 h 3: 52 percent / samarium(II) iodide / tetrahydrofuran; H2O / 18 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: MeONa / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: NaN3 / dimethylformamide / 70 °C 6.1: H2 / Pd/C / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: tetrahydrofuran / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (PhO)2PON3 2: Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: NaN3 / dimethylformamide / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2 1-(Phenylmethyl)-1H-Pyrrole-2-Carboxylic Acid The 5.0 g of oil was combined with 100 ml of ethanol (ethyl alcohol) in a 250 ml round bottom flask. The mixture was heated to reflux then sodium hydroxide (3.0 g) in 15 ml of water was added. The reaction refluxed for 2 hours and was then diluted with 50 ml water. The mixture was cooled in an ice-bath then acidified by addition of 5.0 g of malonic acid. The mixture was then extracted with diethylether in a 500 ml sepratory funnel. The ether layer was washed with water and saturated sodium chloride solution (brine). The ether layer was filtered through sodium sulfate and evaporated to dryness under reduced pressure to give 2.8 g of a brown crystalline solid. The solid was recrystallized from acetonitrile to give 1.3 g of white fluffy crystals of the title compound. mp=130° C. to 133° C. In like manner, by substituting the following starting materials for benzylamine above, and following the procedure in Example 2, the following compounds can be made: | ||
2 1-(Phenylmethyl)-1H-Pyrrole-2-Carboxylic Acid The 5.0 g of oil was combined with 100 ml of ethanol (ethyl alcohol) in a 250 ml round bottom flask. The mixture was heated to reflux then sodium hydroxide (3.0 g) in 15 ml of water was added. The reaction refluxed for 2 hours and was then diluted with 50 ml water. The mixture was cooled in an ice-bath then acidified by addition of 5.0 g of malonic acid. The mixture was then extracted with diethylether in a 500 ml sepratory funnel. The ether layer was washed with water and saturated sodium chloride solution (brine). The ether layer was filtered through sodium sulfate and evaporated to dryness under reduced pressure to give 2.8 g of a brown crystalline solid. The solid was recrystallized from acetonitrile to give 1.3 g of white fluffy crystals of the title compound. mp =130° C. to 133° C. In like manner, by substituting the following starting materials for benzylamine above, and following the procedure in Example 2, the following compounds can be made: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.5% | With water; potassium hydroxide In methanol Reflux; | |
80% | With water; potassium hydroxide In methanol for 3h; Reflux; | |
With methanol; potassium hydroxide; water at 20℃; for 8h; |
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dimethylaluminum chloride In hexane; toluene at 20℃; for 3h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-benzyl-1H-pyrrole; trifluoroacetyl chloride In diethyl ether for 24h; Inert atmosphere; Stage #2: With water; sodium hydroxide In ethanol for 5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.28 g | With thionyl chloride In diethyl ether for 4h; Inert atmosphere; | |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.14% | With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.4% | With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzotriazol-1-ol / dichloromethane / 15.5 h / 0 - 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; potassium hydroxide In methanol at 70℃; for 16h; | 14 Intermediate 2-17.1-l3enzyl-1H-pyrrole-2-carboxylic acid Ethyl 1-benzyl-1H-pyrrole-2-carboxylate (458 mg,2.00 mmol), potassium hydroxide (1.12 g, 20.0 mmol), water(10 mE) and methanol (50 mE) were added to a 100-mEround-bottom flask fitted with a magnetic stir bar, thermometer and condenset The resulting solution was stirred for 16 h at 70° C. The pH of the solution was adjusted to 2 with hydrochloric acid (6.0 M aqueous) and the resulting solution was extracted with ethyl acetate (3x30 mE). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give 1 -benzyl- 1 Hpyrrole-2-carboxylic acid (Intermediate 2-17), which was used in the next step without purification. ECMS: (ESI) mlz 200 [M-H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: potassium hydroxide; water / methanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C 2: dichloromethane / 20 °C 3: N-iodo-succinimide; N-ethyl-N,N-diisopropylamine / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C 2: dichloromethane / 20 °C 3: N-iodo-succinimide; N-ethyl-N,N-diisopropylamine / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
248 mg | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: potassium hydroxide; water / methanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere 3: 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere 3: 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 20 °C 4: copper(II) hexafluoroacetylacetonate / dichloromethane / 16 h / 40 °C / Inert atmosphere |
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