4-Nitrophthalimide → (5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

HRID 523811Notes

Reaction equation

HRID 523811 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][C:13]2=[O:20])([O-:9])=[O:8].[CH2:21]([O:23][C:24](=[O:27])[CH2:25]Br)[CH3:22]>CC(C)=O>[CH2:21]([O:23][C:24](=[O:27])[CH2:25][N:14]1[C:13](=[O:20])[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=2)[C:15]1=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 69694-NitrophthalimideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 784823(5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl esterYield 611.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (57.8 g) was added to a solution mixture of 5-nitro-isoindole-1,3-dione (26.2 g) and bromo-acetic acid ethyl ester (25.1 g) in acetone (500 ml). The resulting mixture was refluxed overnight (18 h). After cooling, reaction mixture was filtered and rinsed with ethyl acetate. Filtrate was concentrated and the residue was triturated with ether (200 ml). Solid was collected and rinsed with ether. Dried in vacuo to give the title compound 231.9 g. 1H NMR (200 MHz, CDCl3) δ 8.69 (m, 2H), 8.07 (d, J=8.2 Hz, 1H), 4.48 (s, 2H), 4.24 (q, J=7.0 Hz, 2H), 1.30 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureThe resulting mixture was refluxed overnight (18 h)
  2. temperatureAfter cooling
  3. customreaction mixture
  4. filtrationwas filtered
  5. washrinsed with ethyl acetate
  6. concentrationFiltrate was concentrated
  7. customthe residue was triturated with ether (200 ml)
  8. customSolid was collected
  9. washrinsed with ether
  10. customDried in vacuo

Sources & evidence

ORD record
ord-5421ce580d354dc9905af997e05a7af7
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

Loading…