Phosphorus oxychloride → 1-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline

HRID 1586185Notes

Reaction equation

HRID 1586185 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([S:18][CH3:19])=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].O=P(Cl)(Cl)[Cl:22]>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:22])=[C:6]2[CH:5]=[N:4]1)=[CH:14][C:15]([S:18][CH3:19])=[CH:16][CH:17]=3)[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21217703N-(1-ethylpyrazol-5-yl)-5-(methylthio)anthranilic acid

Product 1

HCID 212177171-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(1-ethylpyrazol-5-yl)-5-(methylthio) anthranilic acid (4.5 g) and POCl3 (20 ml) is refluxed overnight. The reaction mixture is poured into water, then ice is added. The mixture is extracted with CH2Cl2 and then the CH2Cl2 layer is evaporated. The residue is purified by column chromatography on silica gel eluting with 50% ethyl acetate/hexane to afford 2.4 g of 1-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline, m.p. 120°-121° C.

Workup

  1. temperatureis refluxed overnight
  2. additionice is added
  3. extractionThe mixture is extracted with CH2Cl2
  4. customthe CH2Cl2 layer is evaporated
  5. customThe residue is purified by column chromatography on silica gel eluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f39cf7e402274b348654c062062d4f52
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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