5-Nitrooxindole

Uses

• Reactant for synthesis of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors
• Reactant for preparation of Aurora kinase inhibitors
• Reactant for synthesis of 3-substituted 2-indolinone RET inhibitors
• Reactant for synthesis of 4-azachromeno[2,3-b]indol-11(6H)-ones and derivatives as analogs of ellipticine
• Reactant for preparation of [18F]fluorobenzylidene-indolinone as possible tyrosine kinase inhibitor for PET tumor imaging
• Reactant for preparation of 3-substituted indolin-2-ones as neuroprotective and toxic agents

Synthesis

General procedure for the synthesis of 5-nitroindol-2-one from 2-indolone: 2-indolone (26 g) was dissolved in 100 mL of concentrated sulfuric acid at -15 °C and fuming nitric acid (8.4 mL) was added slowly and dropwise. The reaction temperature needs to be strictly controlled to ensure that it is maintained at -15 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred for 30 minutes. Subsequently, the reaction solution was carefully poured into ice water and a yellow precipitate was immediately generated. The precipitate was separated by filtration and 34 g of 5-nitroindol-2-one was finally obtained in 98% yield.

References

[1] Patent: US2005/256145, 2005, A1. Location in patent: Page/Page column 43
[2] Patent: US2005/256144, 2005, A1. Location in patent: Page/Page column 19
[3] Patent: US2010/75952, 2010, A1. Location in patent: Page/Page column 64
[4] Patent: EP2157093, 2010, A1. Location in patent: Page/Page column 61-62
[5] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 169