Maleic Anhydride → 4-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)-2-(trifluoromethyl)benzonitrile

HRID 2378426Notes

Reaction equation

HRID 2378426 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]#[N:11])[NH2:6].[C:14]1(=O)[O:19][C:17](=[O:18])[CH:16]=[CH:15]1>C(O)(=O)C>[O:18]=[C:17]1[CH:16]=[CH:15][C:14](=[O:19])[N:6]1[C:5]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Product 1

HCID 218749284-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)-2-(trifluoromethyl)benzonitrileYield 61.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-trifluoromethyl-4-cyano-aniline (24.0 g, 129 mmol) and maleic anhydride (14.0 g, 143 mmol) in 50 mL of acetic acid was heated at 115° C. overnight. A precipitate was obtained during the heating period. The reaction was allowed to stand at rt for an additional overnight period. The solid was removed by filtration, the filter cake was washed with diethyl ether and dried to give 21 g (79 mmol, 61%) of compound 471A as an off white solid. HPLC: 100% at 2.11 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 mincontaining 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. customA precipitate was obtained during the heating period
  2. customThe solid was removed by filtration
  3. washthe filter cake was washed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-4d41305fe27d4f7e8dc1a567e0ca3ed9
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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