Water → 1-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline

HRID 375876Notes

Reaction equation

HRID 375876 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][CH:15]=[C:16]([C:18]([OH:20])=[O:19])[CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].O=P(Cl)(Cl)[Cl:23].O>C(O)(=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:23])=[C:6]2[CH:5]=[N:4]1)=[CH:14][CH:15]=[C:16]([C:18]([OH:20])=[O:19])[CH:17]=3)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 21217714N-(1-ethylpyrazol-5-yl)-4-carboxyanthranilic acid

Product 1

HCID 212177041-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of N-(1-ethylpyrazol-5-yl)-4-carboxyanthranilic acid (2.5 g) and POCl3 (20 ml) was refluxed overnight. The reaction mixture was poured into water, acidified with acetic acid and the solids which formed were collected by filtration. The solid was taken up in 10% NaOH, washed with ether and then the aqueous layer was acidified with concentrated HCl. The mixture was extracted with ether, the ether layer was dried over MgSO4 filtered and evaporated to afford 1 g of 1-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline, as a yellow powder.

Workup

  1. temperaturewas refluxed overnight
  2. customthe solids which formed
  3. filtrationwere collected by filtration
  4. washwashed with ether
  5. extractionThe mixture was extracted with ether
  6. dry with materialthe ether layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-09e56ce5e41046f7ba9c313ab7040747
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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