3,4,5,6-Tetrahydrophthalic anhydride → N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1655836Notes

Reaction equation

HRID 1655836 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[F:12][C:13]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:14]=1[NH2:15].O.C1(C)C=CC=CC=1>C(O)(=O)C>[F:12][C:13]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:14]=1[N:15]1[C:1](=[O:11])[C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=2[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 677852-Fluoro-5-nitroanilineHCID 22272177Toluene water

Product 1

HCID 13560456N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4,5,6-tetrahydrophthalic anhydride (22.8 g, 150 mmol), 2-fluoro-5-nitroaniline (23.4 g, 150 mmol) in glacial acetic acid is heated at reflux for 23 hours, cooled and poured into a water/toluene mixture. The organic phase is separated, washed sequentially with water and saturated sodium hydrogen carbonate solution, dried and concentrated in vacuo to obtain a yellow solid. Recrystallization of the solid from ethanol gives the title compound as off-white plates (26.6 g, mp 154°-156° C.) which are identified by 1H and 13C NMR spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 23 hours
  3. temperaturecooled
  4. customThe organic phase is separated
  5. washwashed sequentially with water and saturated sodium hydrogen carbonate solution
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto obtain a yellow solid
  9. customRecrystallization of the solid from ethanol

Sources & evidence

ORD record
ord-bc9929b1aa464d8f962d7ce2a0bdaf47
Source dataset
uspto-grants-1993_10
Patent number
US05252536

Reaction notes

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