Acetic Acid → 4-(4-cyano-1H-imidazol-1-yl)-3-methoxyaniline

HRID 451000Notes

Reaction equation

HRID 451000 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[C:15]([C:17]#[N:18])[N:14]=[CH:13]1.C(O)(=O)C.[OH-].[Na+]>CCO.O.[Fe]>[C:17]([C:15]1[N:14]=[CH:13][N:12]([C:4]2[CH:5]=[CH:6][C:7]([NH2:9])=[CH:8][C:3]=2[O:2][CH3:1])[CH:16]=1)#[N:18]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 667083621-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carbonitrile

Product 1

HCID 667086684-(4-cyano-1H-imidazol-1-yl)-3-methoxyaniline

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carbonitrile (689 mg, 2.82 mmol) in EtOH (Ratio: 2, Volume: 15 mL) was added Acetic Acid (Ratio: 1.000, Volume: 7.50 mL) and Iron (630 mg, 11.29 mmol). The resulting mixture was brought to 100° C. and stirred for 2 h. The reaction was then diluted with water and brought to pH 8 by the addition of 1 N aqueous sodium hydroxide. This mixture was extracted with EtOAc (3×5 mL). The combined extracts were washed with water (5 mL), brine (5 mL), dried over MgSO4, filtered and concentrated in vacuo. LC-MS (M+H)+=215.0.

Workup

  1. customwas brought to 100° C.
  2. extractionThis mixture was extracted with EtOAc (3×5 mL)
  3. washThe combined extracts were washed with water (5 mL), brine (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3edf58bac09d43f89e68c6545921c132
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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