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[ CAS No. 603-62-3 ]

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Chemical Structure| 603-62-3
Chemical Structure| 603-62-3
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CAS No. :603-62-3 MDL No. :MFCD00041852
Formula : C8H4N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :192.13 g/mol Pubchem ID :11779
Synonyms :

Safety of [ 603-62-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 603-62-3 ]

  • Upstream synthesis route of [ 603-62-3 ]
  • Downstream synthetic route of [ 603-62-3 ]

[ 603-62-3 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
95% With hydrogen In DMF (N,N-dimethyl-formamide) at 20 - 50℃; 3-Nitrophthalimide (LOOGR) was taken into a hydrogenation vessel and dissolved using 500ML of dimethylformamide. Raney nickel catalyst (20gr, wet) was added to the solution and subjected to hydrogenation conditions initially at 20-30°C UNDER 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50°C. After the hydrogen uptake is over sample was drawn from the reaction mass and checked for the absence of 3-nitrophthalimide by TLC. The reaction mixture was filtered while hot and the catalyst removed by filtration. Solvent was removed from the filtrate under reduced pressure at 60-80°C. Water (500ML) was added to the residue and the mixture stirred for 20-30MIN. The product was isolated by filtration and dried at 60-70°C to get a yellow crystalline solid of 3-aminophthalimide (80gr, 95percent). Melting point: 262-4°C.
95% With hydrogen In DMF (N,N-dimethyl-formamide) at 20 - 50℃; 3-NITROPHTHALIMIDE (LOOGR) was taken into a hydrogenation kettle and dissolved using 500ML of dimethylformamide. 5percent Palladium/carbon (LOGR, 50percent wet) was added to the solution and subjected to hydrogenation conditions initially at 20-30°C under 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50°C. After the hydrogen uptake was over the reaction mixture was filtered while hot and the catalyst removed by filtration. Solvent was removed from the filtrate under reduced pressure at 60-80°C. Water (500ml) was added to the residue and the mixture stirred for 30min. The product was isolated by filtration and dried at 60-70°C to get 80GR (95percent) of yellow crystalline solid of 3- aminophthalimide. Melting point: 263-4°C.
92.5% With hydrogen In methanol; DMF (N,N-dimethyl-formamide) at 25 - 50℃; 3-Nitrophthalimide (LOOGR) was taken into a beaker and dissolved using 200ML of dimethylformamide and 300ML of methanol. The solution was transferred into a 1L hydrogenation kettle and 20gr of Raney nickel was charged into the kettle. Hydrogenation was carried out initially at 20-40psi and 25-30°C until the exothermic nature was over. Hydrogenation was further continued at 40-60psi pressure and 40-50°C. After checking the completion of reaction by TLC catalyst was removed by filtration and the solvents distilled off from the reaction mixture at 50-60°C. The residue thus obtained was suspended in water (500ML) and filtered off to get a bright yellow crystalline compound of 3-aminophthalimide (78gr, 92.5percent). Melting point: 263-4°C
Reference: [1] MedChemComm, 2016, vol. 7, # 2, p. 292 - 296
[2] Patent: WO2004/43919, 2004, A1, . Location in patent: Page 6
[3] Patent: WO2004/43919, 2004, A1, . Location in patent: Page 7
[4] Patent: WO2004/43919, 2004, A1, . Location in patent: Page 7
[5] Journal of Chemical Research, 2011, vol. 35, # 6, p. 326 - 328
[6] Chemische Berichte, 1903, vol. 36, p. 2496
[7] Journal of the American Chemical Society, 1909, vol. 31, p. 489
[8] Journal of the Chemical Society, 1937, p. 26,31
[9] Journal of the Chemical Society, 1949, p. 3304,3310
[10] Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1261 - 1264
[11] Patent: WO2009/118596, 2009, A2, . Location in patent: Page/Page column 23-24
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Reference: [1] Chemical Communications, 2004, # 20, p. 2338 - 2339
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Reference: [1] Chemische Berichte, 1903, vol. 36, p. 2496
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  • [ 521-31-3 ]
Reference: [1] Journal of Chemical Research, 2011, vol. 35, # 6, p. 326 - 328
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YieldReaction ConditionsOperation in experiment
88% With 1,1'-carbonyldiimidazole In acetonitrile at 80 - 82℃; 4-Nitro-lH-isoindole-l, 3(2H)-dione (117.3 g; Formula IV) followed by 1,1- carbonyldiimidazole (138.1 g) were added to a slurry of 3-aminopiperidine-2,6-dione hydrochloride (100 g, Formula III; obtained in Example 1) in acetonitrile (800 mL) to obtain a reaction mixture. The reaction mixture was heated to reflux at 80°C to 82°C and then stirred for 2 hours. 1,1-Carbonyldiimidazole (19.8 g) was further added to the reaction mixture twice over an interval of one hour. The reaction mixture was cooled to 25 °C to 30°C and then stirred for 30 minutes. The product obtained was filtered and the wet solid obtained was dried at 50°C to 55°C under reduced pressure to obtain the title compound. (0076) Yield: 162 g (88percent)
Reference: [1] Patent: WO2018/154516, 2018, A1, . Location in patent: Page/Page column 8
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Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 13, p. 4445 - 4452
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  • [ 135484-76-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 13, p. 4445 - 4452
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  • [ 1015474-32-4 ]
Reference: [1] Patent: US2012/232100, 2012, A1,
[2] Patent: WO2014/39960, 2014, A1,
[3] Patent: EP2683384, 2015, B1,
[4] Patent: WO2015/200795, 2015, A1,
[5] Patent: WO2016/60702, 2016, A1,
[6] Patent: US9365640, 2016, B2,
[7] Patent: WO2017/24019, 2017, A1,
[8] Patent: WO2017/53555, 2017, A1,
[9] Patent: WO2017/96024, 2017, A1,
[10] Patent: WO2017/117118, 2017, A1,
[11] Patent: WO2018/165142, 2018, A1,
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