Extracurricular laboratory: Synthetic route of C12H11NO3

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H11NO3

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H11NO3

To a stirred solution of acetic anhydride (5.0 mL, 53.0 mmol) and 7.7 wt % phosphorus pentoxide in methanesulfonic acid (Eaton’s Reagent) (5.0 mL, 4.60 mmol) was added 2-(3-oxobutyl)isoindoline-l ,3-dione (1.0 g, 4.60 mmol). The reaction was heated at 70 C and for 8 h. The reaction was allowed to cool to room temperature and maintained overnight. The reaction was diluted with EtOAc, washed with ice cold water, dried (Na2S04), filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (Analogix, SF40-115 g, 20 – 100% EtOAc in hexanes). The pure fractions were combined and evaporated to dryness and triturated with 10% EtOAc in hexanes, filtered and evaporated to dryness to give 2-((2,6-dimethyl-4-oxo-4H-pyran-3- yl)methyl)isoindoline-l,3-dione (290 mg, 1.024 mmol, 22.24 % yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 7.91 – 7.74 (m, 4 H), 6.06 (s, 1 H), 4.54 (s, 2 H), 2.43 (s, 3 H), 2.22 (s, 3 H). MS(ES) [M+H]+ 284.0.

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; DONATELLI, Carla, A.; WO2014/107277; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem