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

HRID 1994106Notes

Reaction equation

HRID 1994106 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 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chloropyridine-2-carbonitrile (20.0 g, 121 mmol, prepared as described by Sakamoto et al. Chem. Pharm. Bull. 1985, 33, 565-571) in MeOH (240 mL), was added sodium methoxide (0.655 g, 12.1 mmol). The reaction mixture was stirred at rt under an atmosphere of argon for 2 h. Ethylene diamine (40.0 mL, 597 mmol) was added to the reaction mixture was stirred at 50° C. for 20 h. The solution was allowed to cool to rt and concentrated. The residue was partitioned between water and DCM. The organic layer was separated, dried over MgSO4, filtered and concentrated to give the desired product as a light brown solid (21.9 g, >99%). LCMS: (FA) ES+ 182.09 (M+1).

Workup

  1. stirringwas stirred at 50° C. for 20 h
  2. temperatureto cool to rt
  3. concentrationconcentrated
  4. customThe residue was partitioned between water and DCM
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ba92373c9e28412f97537f8db96bcdb4
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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