Phthalic Anhydride → 2-(4-bromoanilino)-1H-isoindole-1,3(2H)-dione

HRID 1503734Notes

Reaction equation

HRID 1503734 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12>C(O)(=O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]2[C:14](=[O:15])[C:13]3[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]2=[O:16])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 121574-Bromophenylhydrazine hydrochloride

Product 1

HCID 160443392-(4-bromoanilino)-1H-isoindole-1,3(2H)-dioneYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of (4-bromophenyl)hydrazine hydrochloride (0.5 g, 2.2 mmol) in glacial acetic acid (8 mL) was added phthalic anhydride (0.398 g, 2.690 mmol), and the reaction mixture was stirred at 130° C. for 1 h under a nitrogen atmosphere. The reaction mixture was quenched with satd aq. NaHCO3 solution and filtered to give a solid. Purification by column chromatography (SiO2, 0-10% EtOAc in petroleum ether) afforded the title compound as a solid (60 mg, 84%): mp 205-206° C.; 1H NMR (400 MHz, CDCl3) δ 8.71 (s, 1H), 7.99 (m, 4H), 7.32 (d, J=8.8 Hz, 2H), 6.79 (d, J=8.8 Hz, 2H); ESIMS m/z 314.95 ([M−H]−).

Workup

  1. customThe reaction mixture was quenched with satd aq. NaHCO3 solution
  2. filtrationfiltered
  3. customto give a solid
  4. customPurification by column chromatography (SiO2, 0-10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-50318bd85071490c8bcaf4c544b89e52
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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