Phosphorus oxychloride → HCID 19592216, compound

HRID 1458734Notes

Reaction equation

HRID 1458734 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) is refluxed for 3 hours, then is stirred at room temperature overnight. The excess POCl3 is removed by distillation and then the residue is poured into ice/water. The mixture is neutralized with 35% NaOH and then extracted with CH2Cl2. The CH2Cl2 layer is separated and washed with water, then brine and then is dried over MgSO4, filtered and evaporated. The residue is dissolved in CH2Cl2 and then is 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. temperatureis refluxed for 3 hours
  2. customThe excess POCl3 is removed by distillation
  3. additionthe residue is poured into ice/water
  4. extractionextracted with CH2Cl2
  5. customThe CH2Cl2 layer is separated
  6. washwashed with water
  7. dry with materialbrine and then is dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe residue is dissolved in CH2Cl2
  11. customis purified by column chromatography on silca gel
  12. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-e0d561b768fc4d08a9ef91590590b84d
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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