Maleic Anhydride → 1-(4-bromo-3-methylphenyl)-1H-pyrrole-2,5-dione

HRID 2110399Notes

Reaction equation

HRID 2110399 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[C:10]1(=O)[O:15][C:13](=[O:14])[CH:12]=[CH:11]1>C(O)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]2=[O:15])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 233594-Bromo-3-methylaniline

Product 1

HCID 43796851-(4-bromo-3-methylphenyl)-1H-pyrrole-2,5-dioneYield 74.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

4-Bromo-3-methylaniline (1.55 g, 8.33 mmol) and maleic anhydride (0.898 g, 9.16 mmol) were dissolved in acetic acid (10 mL) and heated at 115° C. for 12 h. The reaction was then cooled to 25° C. and the acetic acid was removed in vacuo. The resulting residue was suspended in 5% K2CO3 (100 mL), stirred for 25 minutes, filtered and rinsed with water. The material was then dried in vacuo to give 1.65 g (6.20 mmol, 74%) of compound 1B as a light brown solid. HPLC: 100% at 2.96 min (retention time) (YMC S5 ODS column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm).

Workup

  1. temperatureThe reaction was then cooled to 25° C.
  2. customthe acetic acid was removed in vacuo
  3. filtrationfiltered
  4. washrinsed with water
  5. customThe material was then dried in vacuo

Sources & evidence

ORD record
ord-3a1ceeef2fb24da69aa30d2045a5a5b1
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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