HCID 58305761, compound → HCID 58305774, compound

HRID 2280331Notes

Reaction equation

HRID 2280331 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-54de3ff2ee9c4f2fb667eac1f0d33969
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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