Ammonium Hydroxide → 4-chloro-1-cyclopentyl-1H-pyrazolo[3,4-b]quinoline

HRID 1586145Notes

Reaction equation

HRID 1586145 reaction equation
[CH:1]1([N:6]2[C:10]([NH:11][C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14](O)=O)=[CH:9][CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+].[OH-].O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:14]1[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=[C:10]2[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:7]=[CH:8][C:9]=12

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 54038843N-(1-cyclopentylpyrazol-5-yl) anthranilic acid

Product 1

HCID 212176854-chloro-1-cyclopentyl-1H-pyrazolo[3,4-b]quinoline

Procedure

A mixture of N-(1-cyclopentylpyrazol-5-yl) anthranilic acid (21 g, 0.0775 mol) and POCl3 (100 ml) is refluxed for 8 hours. The reaction mixture is poured into ice waterl and neutralized with NH4OH. A gum forms which is extracted with CH2Cl2. The CH2Cl2 layer is then washed with water, dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography on silica gel eluting with 40% to 70% CH2Cl2 /hexane to afford 7.5 g of 4-chloro-1-cyclopentyl-1H-pyrazolo[3,4-b]quinoline, m.p. 97°-98° C.

Workup

  1. temperatureis refluxed for 8 hours
  2. additionThe reaction mixture is poured into ice waterl
  3. extractionA gum forms which is extracted with CH2Cl2
  4. washThe CH2Cl2 layer is then washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography on silica gel eluting with 40% to 70% CH2Cl2 /hexane

Sources & evidence

ORD record
ord-be33554663e543fa972a02ce027621b5
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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