Sodium Carbonate → 4-(2-Pyridin-4-yl-imidazol-1-yl)-phenylamine

HRID 1864727Notes

Reaction equation

HRID 1864727 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.C([O-])([O-])=O.[Na+].[Na+]>CCO.Cl.[Fe]>[N:18]1[CH:17]=[CH:16][C:15]([C:11]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH:14]=[CH:13][N:12]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 579747224-[1-(4-nitro-phenyl)-1H-imidazol-2-yl]-pyridine

Product 1

HCID 579747254-(2-Pyridin-4-yl-imidazol-1-yl)-phenylamine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 4-[1-(4-Nitro-phenyl)-1H-imidazol-2-yl]-pyridine (6.16 g, 23.0 mmol) in EtOH (75.0 mL) and 2N HCl (7.0 mL) is added iron powder (325 mesh, 17.40 g, 312 mmol) and refluxed for 1 h. The solution is then cooled to RT and Na2CO3 (4.87 g, 56.0 mmol) is added and the resultant suspension is filtered through a pad of celite (521). The filter cake is then washed with EtOH (100 mL) and the filtrate is concentrated under reduced pressure to a brown solid. The crude sample is then purified by column chromatography (5% MeOH:95% DCM) to afford 4-(2-Pyridin-4-yl-imidazol-1-yl)-phenylamine as a tan solid.

Workup

  1. temperaturerefluxed for 1 h
  2. filtrationthe resultant suspension is filtered through a pad of celite (521)
  3. washThe filter cake is then washed with EtOH (100 mL)
  4. concentrationthe filtrate is concentrated under reduced pressure to a brown solid
  5. customThe crude sample is then purified by column chromatography (5% MeOH:95% DCM)

Sources & evidence

ORD record
ord-c98aa0b3c41a41848cea108636ae5060
Source dataset
uspto-grants-2009_12
Patent number
US07625931B2

Reaction notes

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