HCID 17960600, compound → 2-(4,5-Dihydro-1H-imidazol-2-yl)-6-methylaniline

HRID 1866759Notes

Reaction equation

HRID 1866759 reaction equation
[CH3:1][C:2]1[C:3]([N+:13]([O-])=O)=[C:4]([C:8]2[NH:9][CH2:10][CH2:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1>C(O)C.[OH-].[Pd+2].[OH-]>[NH:12]1[CH2:11][CH2:10][N:9]=[C:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH2:13]

Participants

4

Reactant 1

HCID 17960600HCID 17960600, compound

Product 1

HCID 451209702-(4,5-Dihydro-1H-imidazol-2-yl)-6-methylanilineYield 88.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of the title compound of Step A (0.5 g, 2.44 mmol) in ethanol (50 mL) was added palladium hydroxide (50 mg, 20 wt % on carbon). The flask was twice evacuated and flushed with nitrogen and then twice evacuated and flushed with hydrogen. The mixture was vigorously stirred under a balloon of hydrogen for 3 hours before being evacuated, exposed to air and filtered through a pad of Celite®. The solution was concentrated and filtered through a pad of silica gel, eluting with 5% then 10% methanol in dichloromethane, then 5% triethylamine, 10% methanol, 85% dichloromethane. The material eluting in triethylamine/methanol/dichloromethane was concentrated to give the title compound of Step B (0.38 g) as a light brown oil.

Workup

  1. customThe flask was twice evacuated
  2. customflushed with nitrogen
  3. customtwice evacuated
  4. customflushed with hydrogen
  5. custombefore being evacuated
  6. filtrationfiltered through a pad of Celite®
  7. concentrationThe solution was concentrated
  8. filtrationfiltered through a pad of silica gel
  9. washeluting with 5%
  10. washThe material eluting in triethylamine/methanol/dichloromethane
  11. concentrationwas concentrated

Sources & evidence

ORD record
ord-069e78a4f5dd4e94aef8abb2e44d44fb
Source dataset
uspto-grants-2009_12
Patent number
US07629463B2

Reaction notes

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