| Identification | Back Directory | [Name]
3-nitro-N-acrylphenylamine | [CAS]
17090-15-2 | [Synonyms]
3-nitro-N-acrylphenylamine
N-(3-nitrophenyl)prop-2-enamide
2-Propenamide, N-(3-nitrophenyl)-
3-nitro-N-acrylphenylamine ISO 9001：2015 REACH | [Molecular Formula]
C9H8N2O3 | [MDL Number]
MFCD00595891 | [MOL File]
17090-15-2.mol | [Molecular Weight]
192.17 |
| Hazard Information | Back Directory | [Synthesis]
1. 3-Nitroaniline (6.90 g, 50 mmol) was weighed in a 250 mL round bottom flask, dichloromethane (100 mL) was added as solvent and stirring was initiated.
2. The reaction system was cooled to -78 °C and diisopropylethylamine (12.92 g, 100 mmol) was subsequently added to the reaction system.
3. Acryloyl chloride (6.80 g, 75 mmol) was slowly added dropwise to the reaction system under stirring conditions. 4.
4. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and the reaction was continued with stirring for 2 hours.
5. After completion of the reaction, the solvent was removed by concentration under reduced pressure to give the crude product.
6. The crude product was purified using column chromatography with the eluent being petroleum ether/ethyl acetate (4:1, v/v).
7. The target component was collected and the solvent was removed under reduced pressure to afford N-(3-nitrophenyl)acrylamide (9.6 g, 80% yield) as a yellow solid. | [References]
[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5505 - 5512
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 444 - 455
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4179 - 4186
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 765 - 772
[5] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1847 - 1857 |
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