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

HRID 1072910Notes

Reaction equation

HRID 1072910 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-14d30bb58fc44830812c31e9bdb44c7b
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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