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

HRID 1411420
Notes
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Reaction equation

HRID 1411420 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23925IronCatalyst
HCID 702
Ethanol
Solvent
HCID 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-1351803236ea425789d45ee816f43131
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921514B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes