Water → 4,4'-(1-(4-Fluorophenyl)-1H-pyrrole-2,5-diyl)dianiline

HRID 1429241Notes

Reaction equation

HRID 1429241 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+].O>C(O)C.C1COCC1.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([C:22]3[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=3)=[CH:10][CH:11]=[C:12]2[C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 582268151-(4-Fluorophenyl)-2,5-bis(4-nitrophenyl)-1H-pyrrole

Product 1

HCID 582267494,4'-(1-(4-Fluorophenyl)-1H-pyrrole-2,5-diyl)dianilineYield 127.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2,5-bis(4-nitrophenyl)-1H-pyrrole (1.017 g, 2.496 mmol) in ethanol (15 mL) and THF (15 mL) was added iron powder (0.836 g, 14.98 mmol) followed by ammonium chloride (0.401 g, 7.49 mmol) and water (3.75 mL). The reaction mixture was refluxed for 45 minutes. The reaction mixture was slurry filtered through diatomaceous earth and washed with ethanol. The combined filtrates were concentrated, and the residue purified by column chromatography (gradient elution from 30% to 50% EtOAc:hexanes) to provide 1.09 g (77%) of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 45 minutes
  2. filtrationfiltered through diatomaceous earth
  3. washwashed with ethanol
  4. concentrationThe combined filtrates were concentrated
  5. customthe residue purified by column chromatography (gradient elution from 30% to 50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-6bda67cb055046168484cac3a1c739ee
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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