Phosphorus oxychloride → 4-Chloro-2,3-dimethyl-1H-pyrrolo[3,2-c]pyridine

HRID 1686020Notes

Reaction equation

HRID 1686020 reaction equation
[CH3:1][C:2]1[NH:10][C:9]2[CH:8]=[CH:7][NH:6][C:5](=O)[C:4]=2[C:3]=1[CH3:12].P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:5]1[C:4]2[C:3]([CH3:12])=[C:2]([CH3:1])[NH:10][C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 666866142,3-Dimethyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 714120514-Chloro-2,3-dimethyl-1H-pyrrolo[3,2-c]pyridineYield 43%

Procedure

2,3-dimethyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (6.0 g, 37.0 mmol) prepared in Step 3 was added to phosphorus oxychloride (230 ml). The reaction mixture was refluxed under stirring for 6 hours, cooled to room temperature, and then concentrated under reduced pressure. The resulting residue was dissolved in methanol (200 ml). The obtained solution was alkalized with a saturated ammonia solution in methanol and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate) and recrystallized with ether to give the titled compound as a pale yellow solid. (Yield: 43.0%)

Workup

  1. temperatureThe reaction mixture was refluxed
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in methanol (200 ml)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate)
  6. customrecrystallized with ether

Sources & evidence

ORD record
ord-7add1896011c4110a9ef7eaf0cb2a7b3
Source dataset
uspto-grants-2012_04
Patent number
US08148529B2

Reaction notes

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