4-Nitrophenol → HCID 309726, compound

HRID 1587838Notes

Reaction equation

HRID 1587838 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].[H][H].Br[CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:16][CH2:17][N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 309726HCID 309726, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 2 g) was added to a stirred solution of 4-nitrophenol (7 g) in DMF (100 ml) cooled in an ice-water bath. The mixture was stirred until evolution of hydrogen had ceased and N-(2-bromoethyl)phthalimide (12.6 g) was then added. The mixture was stirred and heated at reflux for 10 hours. The cooled mixture was then added to ice-water (500 ml). The precipitated solid was collected by filtration, washed with water and recrystallised from 95% ethanol to give N-(2-(4-nitrophenoxy)ethyl)phthalimide (9.9 g), as crystalline solid, m.p. 151°-153° C.; NMR 4.15(t, 2H), 4.35(t, 2H), 6.95(m, 2H), 7.74(m, 2H), 7.88(m, 2H), 8.18(m, 2H).

Workup

  1. temperaturecooled in an ice-water bath
  2. temperatureheated
  3. temperatureat reflux for 10 hours
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customrecrystallised from 95% ethanol

Sources & evidence

ORD record
ord-38e28b2b3e474ca09cecd42a1b48d1ee
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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