Phosphorus oxychloride → HCID 9835647, compound

HRID 2119653Notes

Reaction equation

HRID 2119653 reaction equation
[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([N+:16]([O-])=O)[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[N:3]1.P(Cl)(Cl)(Cl)=O>>[NH:16]([C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:5]3[CH:4]=[N:3][N:2]([CH3:1])[C:14]=3[C:13](=[O:15])[C:12]=2[CH:11]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13525012HCID 13525012, compound

Product 1

HCID 9835647HCID 9835647, compoundYield 135.2%

Procedure

A mixture of 1-methyl-7-nitro-1,4-dihydro-9H-pyrazolo[4,3-b]-quinolin-9-one ((Stepanov et. al., Chem. Heterocycl. Compd. (Engl. Transl.), 1985, 21, 905), 0.13 g, 0.53 mmol) and phosphorus oxychloride (3 ml) was refluxed for 3 h. After evaporation, the obtained residue was dissolved in ethyl acetate (100 ml), washed with saturated sodium bicarbonate (50 ml) and dried over sodium sulfate. Removal of solvent gave a residue which was chromatographed on a column of silica gel eluting with ethyl acetate/dichloromethane/hexane (1:4:4) to give 104 mg (78%) of the title compound as a solid.

Workup

  1. temperaturewas refluxed for 3 h
  2. customAfter evaporation
  3. dissolutionthe obtained residue was dissolved in ethyl acetate (100 ml)
  4. washwashed with saturated sodium bicarbonate (50 ml)
  5. dry with materialdried over sodium sulfate
  6. customRemoval of solvent
  7. customgave a residue which
  8. customwas chromatographed on a column of silica gel eluting with ethyl acetate/dichloromethane/hexane (1:4:4)

Sources & evidence

ORD record
ord-35f67169b5394dfab81f2ed3929afd7e
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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