Ethanol → HCID 1356358, compound

HRID 571282Notes

Reaction equation

HRID 571282 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7]2=[O:14])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].CCO>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:7]2=[O:14])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 69694-NitrophthalimideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 1356358HCID 1356358, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitroisoindoline-1,3-dione (2 g, 10.41 mmol) in DMF (10 ml), K2CO3 (1.439 g, 10.41 mmol) and methyl 2-bromoacetate (1.930 ml, 20.82 mmol) were added, and the mixture was reacted under MW irradiation for 2 hr at 140° C. Then the solid K2CO3 was filtered off, the solvent was evaporated and the resulting crude was triturated with EtOH obtaining the title compound as a pale brown solid (1.8 g, 6.82 mmol, 65.5% yield, UPLC-MS purity 90%, MS/ESI+ 265.1 [MH]+) which was used without any additional purification.

Workup

  1. customthe mixture was reacted under MW irradiation for 2 hr at 140° C
  2. filtrationThen the solid K2CO3 was filtered off
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ba32e5388b8e4781b97f9ea3bf27b916
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…