Phosphorus oxychloride → HCID 15290750, compound

HRID 1720259Notes

Reaction equation

HRID 1720259 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[CH:14]=[N:13][NH:12][C:10]3=2)[N:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:17])=O>CN(C)C=O>[Cl:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[CH:14]=[N:13][NH:12][C:10]3=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516374HCID 178516374, compound

Product 1

HCID 15290750HCID 15290750, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9-hydroxy-1H-pyrazolo[3,4-f]quinoline (2.97 g, 16.0 mmol) and phosphorus oxychloride (24.58 g, 160 mmol) at 0° C. was treated with dimethylformamide (DMF) (15.4 ml) dropwise. After addition was complete, the viscous reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was then poured onto ice and the resulting dark brown solution was treated with decolorizing carbon and filtered, and the brown filtrate neutralized with 10M NaOH. The light brown solid which resulted was collected by filtration and air dried giving 9-chloro-1H-pyrazolo[3,4-f]quinoline (1.73 g, 53%).

Workup

  1. additionAfter addition
  2. additionThe mixture was then poured onto ice
  3. additionthe resulting dark brown solution was treated with decolorizing carbon
  4. filtrationfiltered
  5. customThe light brown solid which resulted
  6. filtrationwas collected by filtration and air
  7. customdried

Sources & evidence

ORD record
ord-c0c92b99efdf43a8a4e51623d8550083
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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