Ethylenediamine → 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

HRID 1640104Notes

Reaction equation

HRID 1640104 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.C[O-].[Na+].[CH2:13](N)[CH2:14][NH2:15]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[NH:15][CH2:14][CH2:13][N:9]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 591349594-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chloropyridine-2-carbonitrile (20.0 g, 121 nmuol, prepared as described by Sakamoto et al. Chem. Pharm. Bull. 1985, 33, 565-71) in MeOH (240 mL), was added sodium methoxide (0.655 g, 12.1 mmol). The reaction mixture was allowed to stir at rt under an atmosphere of argon for 2 h. Ethylene diamine (40.0 mL, 597 imol) was added and the mixture was allowed to stir at 50° C. for 20 h. The reaction mixture was allowed to cool to rt and then concentrated. The residue was dissolved in a mixture of water and DCM. The organic layer was separated, dried over MgSO4, filtered and concentrated to give 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine as a light brown solid (21.9 g, >99%). LCMS: (FA) ES+ 182.1.

Workup

  1. stirringto stir at 50° C. for 20 h
  2. temperatureto cool to rt
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of water and DCM
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2e83a610c8b34189a661cbdad5d1688b
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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