5-(4-Nitrophenoxy)-1H-isoindole-1,3(2H)-dione → 5-(4-Aminophenoxy)isoindoline-1,3-dione

HRID 598433Notes

Reaction equation

HRID 598433 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][C:12]3=[O:19])=[CH:6][CH:5]=1)([O-])=O>CC(O)=O.O.[Fe]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][C:12]3=[O:19])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 8675015-(4-Nitrophenoxy)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 8826275-(4-Aminophenoxy)isoindoline-1,3-dioneYield 75%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 5-(4-nitrophenoxy)isoindoline-1,3-dione (0.6 g, 2.11 mmol) in conc. AcOH (12 mL) and water (0.1 mL) was stirred under stream of argon while iron powder (0.59 g, 55.9 mmol) was added slowly. This mixture stirred at room temp. for 72 h, then was diluted with water (25 ml) and extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give 5-(4-aminophenoxy)isoindoline-1,3-dione as a brownish solid (0.4 g, 75%): TLC (50% EtOAc/50% hexane) Rf 0.27; 1H NMR (DMSO-d6) δ 5.14 (br s, 2H), 6.62 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H), 7.03 (d, J=2.1 Hz, 1H), 7.23 (dd, 1H), 7.75 (d, J=8.4 Hz, 1H), 11.02 (s, 1H); HPLC ES-MS m/z 255 ((M+H)+, 100%).

Workup

  1. additionwas added slowly
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2c4694d691a40f9a5a6f649ef685dd6
Source dataset
uspto-grants-2011_03
Patent number
US07897623B2

Reaction notes

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