Phosphorus oxychloride → 4-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 498006Notes

Reaction equation

HRID 498006 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](O)=O)[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:3]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:10]1[C:9]2[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=[C:5]2[N:4]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:3]=[C:2]([CH3:1])[C:6]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 223201402-[[3-Methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid

Product 1

HCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineYield 43%

Procedure

A solution of 2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid (50.2 g, 0.17 mol) in phosphorous oxychloride (120 mL, 1.27 mol) was heated under reflux for 1 hour. The solution was cooled to room temperature and concentrated under reduced pressure, and the residue was poured into iced water. The solution was made basic by the addition of a sodium hydroxide solution, and the organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=98:2) to give the title compound (21.5 g, 43% yield).

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. additionthe residue was poured into iced water
  4. additionThe solution was made basic by the addition of a sodium hydroxide solution
  5. extractionthe organic matter was extracted with chloroform
  6. washThe extract was washed with saturated brine and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography (chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-57b1e7fc2c7b452780c72fa385622bbb
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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