Phosphorus oxychloride → HCID 19592216, compound

HRID 1456018Notes

Reaction equation

HRID 1456018 reaction equation
[CH:1]([N:4]1[C:8]([NH:9][C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12](O)=O)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:21]>>[CH:1]([N:4]1[C:8]2=[N:9][C:10]3[C:11]([C:12]([Cl:21])=[C:7]2[CH:6]=[N:5]1)=[CH:15][CH:16]=[CH:17][CH:18]=3)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19592225HCID 19592225, compound

Product 1

HCID 19592216HCID 19592216, compoundYield 40.9%

Procedure

A mixture of N-(1-isopropylpyrazol-5-yl)anthranilic acid (52 g, 0.212 mol) and POCl3 (436 ml, 4.68 mol) was refluxed for 3 hours, then was stirred at room temperature overnight. The excess POCl3 was removed by distillation and then the residue was poured into ice/water. The mixture was neutralized with 35% NaOH and then extracted with CH2 Cl2. The CH2Cl2 layer was separated and washed with water, then brine and then was dried over MgSO4, filtered and evaporated. The residue was dissolved in CH2Cl2 and then was purified by column chromatography on silca gel eluting with CH2Cl2 to afford 21.3 g (40.9%) of 1-isopropyl-4-chloro-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe excess POCl3 was removed by distillation
  3. additionthe residue was poured into ice/water
  4. extractionextracted with CH2 Cl2
  5. customThe CH2Cl2 layer was separated
  6. washwashed with water
  7. dry with materialbrine and then was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe residue was dissolved in CH2Cl2
  11. customwas purified by column chromatography on silca gel
  12. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-b5213fcb42c2413ab9a709347ded73d4
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

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