No renderable structure data available
C1=CC=C2C(=C1)C(=O)N(C2=O)C3=CC=CC=C3NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(2-aminophenyl)isoindole-1,3-dione |
|---|---|
| IUPAC Name | — |
| CAS Number | 4506-62-1 |
| Database ID | 673676 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(2-aminophenyl)isoindole-1,3-dione (CAS 4506-62-1) 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 673676
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-c989f09d60994ce4bf39516dede15eaaConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8f4fd1f1a9ab42e2a4a52ae9c55083dcConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c989f09d60994ce4bf39516dede15eaaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Phthalimidoaniline (44.0 g, 0.21 moles) and ethyl 2-butyryl-3-ethoxyacrylate (45 g, 0.21 moles) were heated together in fusion for 10 minutes then allowed to cool, forming a tan solid. The ethyl 2-buryryl-3-(2-phthalimidophenylamino)acrylate (83.0 g, 97%) was stirred in ether, filtered and dried under vacuum, m.p 153°-5° C. to cool forming a tan solid filtered dried under vacuum, m.p 153°-5° C.
Source ID: ord-8929377535d145a9aabccc39fa559cd9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of the 2-(2-aminophenyl)isoindole-1,3-dione (360 mg, 1.5 mmol) in acetic acid (20 mL) and water (4 mL) was added dropwise a solution of sodium nitrite (98 mg, 1.42 mmol) in water (2 mL). The mixture was allowed to stir for 10 minutes and then sodium azide (98 mg, 1.51 mmol) was added. The reaction mixture was stirred for 15 minutes before it was poured into water and was extracted with dichloromethane (3×50 mL). The extracts were washed with water and brine and dried over magnesium sulfate. Filtration and concentration in vacuo gave 373 mg (94%) of 2-(2-azidophenyl)isoindole-1,3-dione as a solid: 1H NMR (300 MHz, DMSO-d6) δ 7.94 (m, 4H), 7.58 (m, 1H), 7.48 (m, 2H), 7.32 (m, 1H). The reaction mixture was stirred for 15 minutes before it was extracted with dichloromethane (3×50 mL) The extracts were washed with water and brine dried over magnesium sulfate Filtration and concentration in vacuo
Source ID: ord-98b43f9de2bb48838c56a68050b6a42cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of the 2-(2-nitrophenyl)isoindole-1,3-dione (1.0 g, 3.50 mmol) in benzene, pre-sparged with nitrogen gas, was added 10% palladium on activated carbon (1.0 g). The reaction mixture was placed under an atmosphere of hydrogen gas and was vigorously stirred. After 45 minutes, the reaction mixture was filtered over celite and the filter pad was washed with benzene. Concentration in vacuo gave 236 mg (40%) of 2-(2-aminophenyl)-isoindole-1,3-dione as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.85 (m, 4H), 7.10 (m, 1H), 6.98 (m, 1H), 6.75 (m, 1H), 6.55 (m, 1H). pre-sparged with nitrogen gas was added 10% palladium on activated carbon (1.0 g) the reaction mixture was filtered over celite the filter pad was washed with benzene Concentration in vacuo
Source ID: ord-2ea360f61f494f539fd7449e40c062faConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8f4fd1f1a9ab42e2a4a52ae9c55083dcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of the 2-(2-aminophenyl)isoindole-1,3-dione (360 mg, 1.5 mmol) in acetic acid (20 mL) and water (4 mL) was added dropwise a solution of sodium nitrite (98 mg, 1.42 mmol) in water (2 mL). The mixture was allowed to stir for 10 minutes and then sodium azide (98 mg, 1.51 mmol) was added. The reaction mixture was stirred for 15 minutes before it was poured into water and was extracted with dichloromethane (3×50 mL). The extracts were washed with water and brine and dried over magnesium sulfate. Filtration and concentration in vacuo gave 373 mg (94%) of 2-(2-azidophenyl)isoindole-1,3-dione as a solid: 1H NMR (300 MHz, DMSO-d6) δ 7.94 (m, 4H), 7.58 (m, 1H), 7.48 (m, 2H), 7.32 (m, 1H). The reaction mixture was stirred for 15 minutes before it was extracted with dichloromethane (3×50 mL) The extracts were washed with water and brine dried over magnesium sulfate Filtration and concentration in vacuo
Source ID: ord-d314b9f4286845858dcb5334a50af38aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of the 2-(2-nitrophenyl)isoindole-1,3-dione (1.0 g, 3.50 mmol) in benzene, pre-sparged with nitrogen gas, was added 10% palladium on activated carbon (1.0 g). The reaction mixture was placed under an atmosphere of hydrogen gas and was vigorously stirred. After 45 minutes, the reaction mixture was filtered over celite and the filter pad was washed with benzene. Concentration in vacuo gave 236 mg (40%) of 2-(2-aminophenyl)-isoindole-1,3-dione as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.85 (m, 4H), 7.10 (m, 1H), 6.98 (m, 1H), 6.75 (m, 1H), 6.55 (m, 1H). pre-sparged with nitrogen gas was added 10% palladium on activated carbon (1.0 g) the reaction mixture was filtered over celite the filter pad was washed with benzene Concentration in vacuo
Source ID: ord-0c75ce1b22c946ea89fb0c570c4d3a2cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Phthalimidoaniline (44.0 g, 0.21 moles) and ethyl 2-butyryl-3-ethoxyacrylate (45 g, 0.21 moles) were heated together in fusion for 10 minutes then allowed to cool, forming a tan solid. The ethyl 2-buryryl-3-(2-phthalimidophenylamino)acrylate (83.0 g, 97%) was stirred in ether, filtered and dried under vacuum, m.p 153°-5° C. to cool forming a tan solid filtered dried under vacuum, m.p 153°-5° C.
Source ID: ord-8929377535d145a9aabccc39fa559cd9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of the 2-(2-aminophenyl)isoindole-1,3-dione (360 mg, 1.5 mmol) in acetic acid (20 mL) and water (4 mL) was added dropwise a solution of sodium nitrite (98 mg, 1.42 mmol) in water (2 mL). The mixture was allowed to stir for 10 minutes and then sodium azide (98 mg, 1.51 mmol) was added. The reaction mixture was stirred for 15 minutes before it was poured into water and was extracted with dichloromethane (3×50 mL). The extracts were washed with water and brine and dried over magnesium sulfate. Filtration and concentration in vacuo gave 373 mg (94%) of 2-(2-azidophenyl)isoindole-1,3-dione as a solid: 1H NMR (300 MHz, DMSO-d6) δ 7.94 (m, 4H), 7.58 (m, 1H), 7.48 (m, 2H), 7.32 (m, 1H). The reaction mixture was stirred for 15 minutes before it was extracted with dichloromethane (3×50 mL) The extracts were washed with water and brine dried over magnesium sulfate Filtration and concentration in vacuo
Source ID: ord-98b43f9de2bb48838c56a68050b6a42cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of the 2-(2-nitrophenyl)isoindole-1,3-dione (1.0 g, 3.50 mmol) in benzene, pre-sparged with nitrogen gas, was added 10% palladium on activated carbon (1.0 g). The reaction mixture was placed under an atmosphere of hydrogen gas and was vigorously stirred. After 45 minutes, the reaction mixture was filtered over celite and the filter pad was washed with benzene. Concentration in vacuo gave 236 mg (40%) of 2-(2-aminophenyl)-isoindole-1,3-dione as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.85 (m, 4H), 7.10 (m, 1H), 6.98 (m, 1H), 6.75 (m, 1H), 6.55 (m, 1H). pre-sparged with nitrogen gas was added 10% palladium on activated carbon (1.0 g) the reaction mixture was filtered over celite the filter pad was washed with benzene Concentration in vacuo
Source ID: ord-2ea360f61f494f539fd7449e40c062faPubChem References
These sources are listed in the compound's public database record.
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