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C1=CC=C(C=C1)C=CC(=O)NC2=CC=CC=C2BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-(2-bromophenyl)-3-phenylprop-2-enamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 71910-51-5 |
| Database ID | 764332 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-(2-bromophenyl)-3-phenylprop-2-enamide (CAS 71910-51-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 764332
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-12ee68e32bcd4b29ae205e1729c312c1Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(2-bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 100° C. for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected. by cooling to ambient temperature overnight to warm to ambient temperature over 1 hour The resulting mixture was extracted with dichloromethane The combined organic layers were dried over MgSO4 concentrated under reduced pressure The resulting solids were triturated with 1000 ml hexanes dried
Source ID: ord-b6c5860b1e9b4a00b921c599e6b0883cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-bromobenzenamine (200.0 g, 1163 mmol), pyridine (188.1 ml, 2325 mmol) and dry dichloromethane (1000 ml) at 0° C. was added slowly cinnamoyl chloride (193.7 g, 1163 mmol). The resulting mixture was stirred while warming to ambient temperature overnight. The resulting mixture was washed with sodium bicarbonate (1000 ml), 10% sodium bisulfate (1000 ml), sodium bicarbonate (1000 ml) and brine (1000 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to yield title compound as a solid (172.3 gm, 98% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected. The resulting mixture was washed with sodium bicarbonate (1000 ml), 10% sodium bisulfate (1000 ml), sodium bicarbonate (1000 ml) and brine (1000 ml) The organic layer was dried over MgSO4 concentrated under reduced pressure
Source ID: ord-663da7ac9a59420ba1f1efdc76a512b6Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Aluminum chloride (2.6 g, 19.92 mmol) was added to a solution of N-(2-bromophenyl)cinnamamide (1.0 g, 3.32 mmol) in chlorobenzene, and the resulting mixture was heated at 125° C. for 2 h. The reaction mixture was then cooled to 50° C. and treated with ice-cold water (25 mL) to provide a brown precipitate. The precipitate was collected by vacuum filtration and dried in vacuo, then triturated with EtOH to provide 8-bromoquinolin-2(1H)-one (0.5 g, 67% yield) as an off-white solid. m/z (ESI, +ve) 226.2 (M+H)+ The reaction mixture was then cooled to 50° C. to provide a brown precipitate The precipitate was collected by vacuum filtration dried in vacuo triturated with EtOH
Source ID: ord-70bde04703204b5fb871d7eb38a46c36Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-bromoaniline (0.976 g, 5.81 mmol, Sigma-Aldrich) and K2CO3 (1.16 g, 8.71 mmol) in water (5.5 mL) and acetone (4.5 mL) was added cinnamoyl chloride (1 g, 5.81 mmol, Sigma-Aldrich) and the reaction was stirred for 2 h at 0° C. The mixture was treated with ice cold water (25 mL) to obtain a brownish precipitate. The precipitate was filtered and dried under vacuum. The crude material was further treated with petroleum ether to give N-(2-bromophenyl)cinnamamide (1.1 g, 64%) as off-white solid. MS (ESI, pos. ion) m/z: 303.2 (M+1). to obtain a brownish precipitate The precipitate was filtered dried under vacuum The crude material was further treated with petroleum ether
Source ID: ord-e5bccb47e001461dbbdf352ff3cb302aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-bromoaniline (0.976 g, 5.81 mmol, Sigma-Aldrich) and K2CO3 (1.16 g, 8.71 mmol) in water (5.5 mL) and acetone (4.5 mL) was added cinnamoyl chloride (1 g, 5.81 mmol, Sigma-Aldrich) and the reaction was stirred for 2 h at 0° C. The mixture was treated with ice cold water (25 mL) to obtain a brownish precipitate. The precipitate was filtered and dried under vacuum. The crude material was further treated with petroleum ether to give N-(2-bromophenyl)cinnamamide (1.1 g, 64%) as off-white solid. MS (ESI, pos. ion) m/z: 303.2 (M+1). to obtain a brownish precipitate The precipitate was filtered dried under vacuum The crude material was further treated with petroleum ether
Source ID: ord-e5bccb47e001461dbbdf352ff3cb302aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-12ee68e32bcd4b29ae205e1729c312c1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Bromoaniline (48.41 g, 281.4 mMol) was dissolved in 500 mL of anhydrous DCM under an atmosphere of dry N2. Pyridine (45.5 mL, 563 mMol) was then added and the reaction was subsequently cooled to 0° C. after which time cinnamyl chloride (46.9 g, 281.4 mMol) was added. The reaction mixture was slowly warmed up to ambient temperature and then stirred overnight at ambient temperature. The reaction was diluted with 300 mL of saturated aqueous NaHCO3 and then extracted with DCM. The DCM layer was then washed three times with 10% aqueous NaHSO4 followed by saturated aqueous NaHCO3 and finally brine. The DCM layer was then dried over Na2SO4, filtered and concentrated under vacuum to give 85.08 g of a tan solid as the title compound 61A. was added extracted with DCM The DCM layer was then washed three times with 10% aqueous NaHSO4 The DCM layer was then dried over Na2SO4 filtered concentrated under vacuum
Source ID: ord-f71303a962894eb5b2b69c7a4e1a2188Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(2-bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 100° C. for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected. by cooling to ambient temperature overnight to warm to ambient temperature over 1 hour The resulting mixture was extracted with dichloromethane The combined organic layers were dried over MgSO4 concentrated under reduced pressure The resulting solids were triturated with 1000 ml hexanes dried
Source ID: ord-b6c5860b1e9b4a00b921c599e6b0883cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-bromobenzenamine (200.0 g, 1163 mmol), pyridine (188.1 ml, 2325 mmol) and dry dichloromethane (1000 ml) at 0° C. was added slowly cinnamoyl chloride (193.7 g, 1163 mmol). The resulting mixture was stirred while warming to ambient temperature overnight. The resulting mixture was washed with sodium bicarbonate (1000 ml), 10% sodium bisulfate (1000 ml), sodium bicarbonate (1000 ml) and brine (1000 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to yield title compound as a solid (172.3 gm, 98% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected. The resulting mixture was washed with sodium bicarbonate (1000 ml), 10% sodium bisulfate (1000 ml), sodium bicarbonate (1000 ml) and brine (1000 ml) The organic layer was dried over MgSO4 concentrated under reduced pressure
Source ID: ord-663da7ac9a59420ba1f1efdc76a512b6Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Aluminum chloride (2.6 g, 19.92 mmol) was added to a solution of N-(2-bromophenyl)cinnamamide (1.0 g, 3.32 mmol) in chlorobenzene, and the resulting mixture was heated at 125° C. for 2 h. The reaction mixture was then cooled to 50° C. and treated with ice-cold water (25 mL) to provide a brown precipitate. The precipitate was collected by vacuum filtration and dried in vacuo, then triturated with EtOH to provide 8-bromoquinolin-2(1H)-one (0.5 g, 67% yield) as an off-white solid. m/z (ESI, +ve) 226.2 (M+H)+ The reaction mixture was then cooled to 50° C. to provide a brown precipitate The precipitate was collected by vacuum filtration dried in vacuo triturated with EtOH
Source ID: ord-70bde04703204b5fb871d7eb38a46c36Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-bromoaniline (0.976 g, 5.81 mmol, Sigma-Aldrich) and K2CO3 (1.16 g, 8.71 mmol) in water (5.5 mL) and acetone (4.5 mL) was added cinnamoyl chloride (1 g, 5.81 mmol, Sigma-Aldrich) and the reaction was stirred for 2 h at 0° C. The mixture was treated with ice cold water (25 mL) to obtain a brownish precipitate. The precipitate was filtered and dried under vacuum. The crude material was further treated with petroleum ether to give N-(2-bromophenyl)cinnamamide (1.1 g, 64%) as off-white solid. MS (ESI, pos. ion) m/z: 303.2 (M+1). to obtain a brownish precipitate The precipitate was filtered dried under vacuum The crude material was further treated with petroleum ether
Source ID: ord-e5bccb47e001461dbbdf352ff3cb302aPubChem References
These sources are listed in the compound's public database record.
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