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

HRID 2364776Notes

Reaction equation

HRID 2364776 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 example 19A (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). Reaction mixture was refluxed for 45 minutes. Slurry filtered through celite, washed with ethanol, combined filtrate was 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. customReaction mixture
  2. temperaturewas refluxed for 45 minutes
  3. filtrationSlurry filtered through celite
  4. washwashed with ethanol
  5. concentrationwas concentrated
  6. customthe residue purified by column chromatography (gradient elution from 30% to 50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-c31cad0c889c4a35ac1c242e30c19f26
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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