No renderable structure data available
C1=CC=C(C=C1)C=CC(=O)NC2=CC=CC=C2FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-(2-fluorophenyl)-3-phenylprop-2-enamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 25893-50-9 |
| Database ID | 303250 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-(2-fluorophenyl)-3-phenylprop-2-enamide (CAS 25893-50-9) 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 303250
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-f2e7028c4e3c4672bab399bbc1d0afb6Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-Fluorophenyl)cinnamamide (10.5 g, 44 mmol) was dissolved in chloro-benzene (60 mL) and aluminum trichloride (29.0 g, 218 mmol, 5 eq) was added. The reaction was heated to 125° C. for 3 h and then cooled to rt over 45 min. The reaction was poured onto 300 g of ice with stirring, producing a tan solid. The solid was filtered and washed with 100 mL of water and 3×100 mL of hexanes and dried under high vacuum. The solid was extracted with 1 L of DCM and filtered to remove insoluble byproducts. The solvent was removed in vacuo to afford 8-fluoroquinolin-2(1H)-one. 1H NMR (400 MHz, CDCl3) δ ppm 10.95 (br s, 1H), 7.77 (dd, J=9.8, 1.6 Hz, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.27 (ddd, J=10.2, 7.8, 1.2 Hz, 1H), 7.14 (td, J=8.0, 5.1 Hz, 1H), 6.76 (d, J=9.4 Hz, 1H). cooled to rt over 45 min producing a tan solid The solid was filtered washed with 100 mL of water and 3×100 mL of hexanes dried under high vacuum The solid was extracted with 1 L of DCM filtered to remove insoluble byproducts The solvent was removed in vacuo
Source ID: ord-9197971088144efaba979bc23a7af862Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-fluoroaniline (25.0 g, 225 mmol) and potassium carbonate (47 g, 337 mmol) in water (112 mL) and acetone (45 mL) at 0° C. was added cinnamoyl chloride (37.0 g, 225 mmol, 1 eq) in acetone (45 mL) over 2 h. The reaction was stirred for 1 h at 0° C., and quenched into 200 mL of ice-water. The white crystalline solid was filtered and washed with water. The solid was air dried for 2 h, then washed with 400 mL of hexanes. The solid was dried under vacuum overnight to afford N-(2-fluorophenyl)cinnamamide (56 g, 103% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.49 (br t, J=7.8 Hz, 1H), 7.80 (d, J=15.3 Hz, 1H), 7.57 (m, 3H), 7.41 (m, 3H), 7.17 (m, 3H), 6.61 (d, J=15.6 Hz, 1H). Mass Spectrum (ESI) m/e=242.1 (M+1). quenched into 200 mL of ice-water The white crystalline solid was filtered washed with water dried for 2 h washed with 400 mL of hexanes The solid was dried under vacuum overnight
Source ID: ord-63518db6d3f44171bbac0f372ffad46dConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-fluoroaniline (25.0 g, 225 mmol) and potassium carbonate (47 g, 337 mmol) in water (112 mL) and acetone (45 mL) at 0° C. was added cinnamoyl chloride (37.0 g, 225 mmol, 1 eq) in acetone (45 mL) over 2 h. The reaction was stirred for 1 h at 0° C., and quenched into 200 mL of ice-water. The white crystalline solid was filtered and washed with water. The solid was air dried for 2 h, then washed with 400 mL of hexanes. The solid was dried under vacuum overnight to afford N-(2-fluorophenyl)cinnamamide (56 g, 103% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.49 (br t, J=7.8 Hz, 1H), 7.80 (d, J=15.3 Hz, 1H), 7.57 (m, 3H), 7.41 (m, 3H), 7.17 (m, 3H), 6.61 (d, J=15.6 Hz, 1H). Mass Spectrum (ESI) m/e=242.1 (M+1). quenched into 200 mL of ice-water The white crystalline solid was filtered washed with water dried for 2 h washed with 400 mL of hexanes The solid was dried under vacuum overnight
Source ID: ord-63518db6d3f44171bbac0f372ffad46dConditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-Fluorophenyl)cinnamamide (97.2 g, 403 mmol) was combined with AlCl3 (161 g, 1209 mmol) and the solids were thoroughly mixed. The dry mixture was heated to 160° C. for 100 minutes. The reaction was cooled and quenched by addition of ice. A beige solid formed after complete dispersion of the dark solids and this was stirred overnight. The beige solid was filtered and air-dried overnight to provide the desired product as a free-flowing solid (69.8 g). the solids were thoroughly mixed The reaction was cooled quenched by addition of ice A beige solid formed after complete dispersion of the dark solids The beige solid was filtered air-dried overnight
Source ID: ord-4be856c419ca4821815d734889a0a8dcConditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-Fluorophenyl)cinnamamide (97.2 g, 403 mmol) was combined with AlCl3 (161 g, 1209 mmol) and the solids were thoroughly mixed. The dry mixture was heated to 160° C. for 100 minutes. The reaction was cooled and quenched by addition of ice. A beige solid formed after complete dispersion of the dark solids and this was stirred overnight. The beige solid was filtered and air-dried overnight to provide the desired product as a free-flowing solid (69.8 g). the solids were thoroughly mixed The reaction was cooled quenched by addition of ice A beige solid formed after complete dispersion of the dark solids The beige solid was filtered air-dried overnight
Source ID: ord-4be856c419ca4821815d734889a0a8dcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Cinnamoyl chloride (89.2 g, 535 mmol) was dissolved in THF (170 mL) and added dropwise to a 0° C. solution of 2-fluoroaniline (54.1 g, 486 mmol) and pyridine (39.35 mL, 486.5 mmol) dissolved in THF (170 mL). The mixture was allowed to warm to ambient temperature after the addition and stirred for 15 hours. A solution of 2M HCl was added (1250 mL) and the mixture was stirred at ambient temperature for 8 hours, during which the initial oil solidified to a light pink solid. This material was collected by filtration, washed with several portions of water, and air-dried to provide the desired product (119.5 g). after the addition the mixture was stirred at ambient temperature for 8 hours, during which the initial oil This material was collected by filtration washed with several portions of water air-dried
Source ID: ord-e420f71d5d044733beb6ebca854090f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-Fluorophenyl)cinnamamide (10.5 g, 44 mmol) was dissolved in chlorobenzene (60 mL) and aluminum trichloride (29 g, 218 mmol, 5 eq) was added. The reaction was heated to 125 C for 3 h and then cooled to rt over 45 minutes. The reaction was poured onto 300 g of ice with stirring, producing a tan solid. The solid was filtered and washed with 100 mL of water and 3×100 mL of hexanes and dried under high vacuum. The solid was extracted with 1 L of DCM and filtered to remove insoluble byproducts. The solvent was removed in vacuo to afford 8-fluoroquinolin-2(1H)-one. 1H NMR (400 MHz, CDCl3) δ ppm 10.95 (br s, 1H), 7.77 (dd, J=9.8, 1.6 Hz), 7.35 (d, J=7.8 Hz, 1H), 7.27 (ddd, J=10.2, 7.8, 1.2 Hz, 1H), 7.14 (td, J=8.0, 5.1 Hz, 1H), 6.76 (d, J=9.4 Hz, 1H). The reaction was heated to 125 C for 3 h producing a tan solid The solid was filtered washed with 100 mL of water and 3×100 mL of hexanes dried under high vacuum The solid was extracted with 1 L of DCM filtered to remove insoluble byproducts The solvent was removed in vacuo
Source ID: ord-77d2116ad8b84d239595eb725bec7715Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-fluoroaniline (25.0 g, 225 mmol) and potassium carbonate (47 g, 337 mmol) in water (112 mL) and acetone (45 mL) at 0° C. was added cinnamoyl chloride (37 g, 225 mmol, 1 eq) in acetone (45 mL) over 2 h. The reaction was stirred for 1 h (0° C., then quenched into 200 mL of ice-water. The white crystalline solid was filtered and washed with water. The solid was air dried for 2 h, then washed with 400 mL of hexanes. The solid was dried under vacuum overnight to afford product. 1H NMR (400 MHz, CDCl3) δ ppm 8.49 (br t, J=7.8 Hz, 1H), 7.80 (d, J=15.3 Hz, 1H), 7.57 (m, 3H), 7.41 (m, 3H), 7.17 (m, 3H), 6.61 (d, J=15.6 Hz, 1H). Mass Spectrum (ESI) m/e=242.1 (M+1). quenched into 200 mL of ice-water The white crystalline solid was filtered washed with water dried for 2 h washed with 400 mL of hexanes The solid was dried under vacuum overnight to afford product
Source ID: ord-2c96ab7bfbaa44ca9300fbe2345bb29bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(2-Fluorophenyl)cinnamamide (10.5 g, 44 mmol) was dissolved in chlorobenzene (60 mL) and aluminum trichloride (29 g, 218 mmol, 5 eq) was added. The reaction was heated to 125 C for 3 h and then cooled to rt over 45 minutes. The reaction was poured onto 300 g of ice with stirring, producing a tan solid. The solid was filtered and washed with 100 mL of water and 3×100 mL of hexanes and dried under high vacuum. The solid was extracted with 1 L of DCM and filtered to remove insoluble byproducts. The solvent was removed in vacuo to afford 8-fluoroquinolin-2(1H)-one. 1H NMR (400 MHz, CDCl3) δ ppm 10.95 (br s, 1H), 7.77 (dd, J=9.8, 1.6 Hz), 7.35 (d, J=7.8 Hz, 1H), 7.27 (ddd, J=10.2, 7.8, 1.2 Hz, 1H), 7.14 (td, J=8.0, 5.1 Hz, 1H), 6.76 (d, J=9.4 Hz, 1H). The reaction was heated to 125 C for 3 h producing a tan solid The solid was filtered washed with 100 mL of water and 3×100 mL of hexanes dried under high vacuum The solid was extracted with 1 L of DCM filtered to remove insoluble byproducts The solvent was removed in vacuo
Source ID: ord-77d2116ad8b84d239595eb725bec7715Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-fluoroaniline (25.0 g, 225 mmol) and potassium carbonate (47 g, 337 mmol) in water (112 mL) and acetone (45 mL) at 0° C. was added cinnamoyl chloride (37 g, 225 mmol, 1 eq) in acetone (45 mL) over 2 h. The reaction was stirred for 1 h (0° C., then quenched into 200 mL of ice-water. The white crystalline solid was filtered and washed with water. The solid was air dried for 2 h, then washed with 400 mL of hexanes. The solid was dried under vacuum overnight to afford product. 1H NMR (400 MHz, CDCl3) δ ppm 8.49 (br t, J=7.8 Hz, 1H), 7.80 (d, J=15.3 Hz, 1H), 7.57 (m, 3H), 7.41 (m, 3H), 7.17 (m, 3H), 6.61 (d, J=15.6 Hz, 1H). Mass Spectrum (ESI) m/e=242.1 (M+1). quenched into 200 mL of ice-water The white crystalline solid was filtered washed with water dried for 2 h washed with 400 mL of hexanes The solid was dried under vacuum overnight to afford product
Source ID: ord-2c96ab7bfbaa44ca9300fbe2345bb29bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f2e7028c4e3c4672bab399bbc1d0afb6PubChem References
These sources are listed in the compound's public database record.
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