Stannous Chloride → ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylate

HRID 842698Notes

Reaction equation

HRID 842698 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[Sn](Cl)Cl>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 18726773ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylate

Product 1

HCID 18726772ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-nitrophenyl)imidazole-4-carboxylic acid ethyl ester (see part (i)) (950 mg, 3.64 mmol) and tin (II) chloride (4.11 g, 18.2 mmol) in absolute ethanol (30 ml) was heated under reflux for 30 minutes under nitrogen. After cooling to room temperature the mixture was concentrated under reduced pressure and then partitioned between ethyl acetate (30 ml) and saturated sodium hydrogen carbonate solution (20 ml). The aqueous layer was extracted with ethyl acetate (30 ml) and the combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give 1-(4-aminophenyl)imidazole-4-carboxylic acid ethyl ester (810 mg, 96%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes under nitrogen
  3. concentrationwas concentrated under reduced pressure
  4. custompartitioned between ethyl acetate (30 ml) and saturated sodium hydrogen carbonate solution (20 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (30 ml)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-196bf49671e247bcb6b951e48f55f228
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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