Chloroform → 5-Chloro-2,7-dimethyl-1H-imidazo[4,5-b]pyridine

HRID 1699930Notes

Reaction equation

HRID 1699930 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:5]([N:12]=1)=[N+:6]([O-])[CH:7]=[CH:8][C:9]=2[CH3:10].C(Cl)(Cl)[Cl:14]>P(Cl)(Cl)(Cl)=O>[Cl:14][C:7]1[N:6]=[C:5]2[N:12]=[C:2]([CH3:1])[NH:3][C:4]2=[C:9]([CH3:10])[CH:8]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 178432335HCID 178432335, compound

Product 1

HCID 223884515-Chloro-2,7-dimethyl-1H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,7-dimethyl-1H-imidazo[4,5-b]pyridine-4-oxide (4.45 g) in chloroform (4.5 ml) and phosphorous oxychloride (25.4 ml) was stirred at 80° C. for 3 hr and concentrated to dryness under reduced pressure. The residue was poured to ice (75 g), and which was neutralized with aqueous ammonia under ice-cooling. The mixture was stirred at room temperature for 30 min and the precipitated solid was washed with water to give the objective compound (3.66 g) as a gray powder.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. additionThe residue was poured to ice (75 g), and which
  3. temperaturecooling
  4. stirringThe mixture was stirred at room temperature for 30 min
  5. washthe precipitated solid was washed with water

Sources & evidence

ORD record
ord-35a1294807654fea90fd7894e0a03e00
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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