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

HRID 375861Notes

Reaction equation

HRID 375861 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) was refluxed for 8 hours. The reaction mixture was poured into ice-water and neutralized with NH4OH. A gum formed which was extracted with CH2Cl2. The CH2Cl2 layer was then washed with water, dried over MgSO4, filtered and concentrated. The residue was 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. temperaturewas refluxed for 8 hours
  2. customA gum formed which
  3. extractionwas extracted with CH2Cl2
  4. washThe CH2Cl2 layer was then washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel eluting with 40% to 70% CH2Cl2 /hexane

Sources & evidence

ORD record
ord-a15b818f7b4240d481200d72de8a935f
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

Loading…