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

HRID 1406229Notes

Reaction equation

HRID 1406229 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]>>[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

4

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%

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 actone (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, 2 H), 8.07 (d, J=8.2 Hz, 1 H), 4.48 (s, 2 H), 4.24 (q, J=7.0 Hz, 2 H), 1.30 (t, J=7.0 Hz, 3 H).

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-47e6cfd6ce8242c2b346750229bb5eef
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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