HCID 58305761, compound → HCID 58305774, compound

HRID 2362253Notes

Reaction equation

HRID 2362253 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CCO.CO.[Pd]>[NH:12]1[CH:13]=[CH:14][N:15]=[C:11]1[C:4]1[CH:5]=[CH:6][C:7]([NH2:8])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 1

HCID 58305761HCID 58305761, compound

Product 1

HCID 58305774HCID 58305774, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a mixture of 2-(3-methyl-4-nitrophenyl)-1H-imidazole (1.17 g, 5.76 mmol) and 10% Pd/C (0.8 g) in EtOH (5 mL) was added dropwise HCO2NH4 [3.63 g, 57.64 mmol., dissolving in MeOH (50 mL)]. After 1 h, TLC showed the reaction was complete. Filtration and the filtrate was evaporated under reduced pressure. The residue was dissolved in DCM (30 mL) and filtrated. The filtrate was concentrated to afford 4-(1H-imidazol-2-yl)-2-methylaniline as a yellow solid (1.0 g, 99%).

Workup

  1. filtrationFiltration
  2. customthe filtrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (30 mL)
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d11d3a6cb29a495793e980b02ff4d686
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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