Ammonium Hydroxide → 1-isopropyl-6-(diethylaminosulfonyl)-4-chloro-1H-pyrazolo[3,4-b]quinoline

HRID 375899Notes

Reaction equation

HRID 375899 reaction equation
[CH:1]([N:4]1[C:8]([NH:9][C:10]2[C:11](=[CH:15][C:16]([S:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])(=[O:21])=[O:20])=[CH:17][CH:18]=2)[C:12](O)=O)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:31]>>[CH:1]([N:4]1[C:8]2=[N:9][C:10]3[C:11]([C:12]([Cl:31])=[C:7]2[CH:6]=[N:5]1)=[CH:15][C:16]([S:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])(=[O:21])=[O:20])=[CH:17][CH:18]=3)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 54426707N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acid

Product 1

HCID 212177161-isopropyl-6-(diethylaminosulfonyl)-4-chloro-1H-pyrazolo[3,4-b]quinoline

Procedure

A mixture of N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acid (12.0 g, 0.031 mol) and POCl3 (80 mL) was refluxed for 6 hours. The reaction mixture was cooled to room temperature and then was poured into ice-water and neutralized with concentrated NH4OH. The mixture was extracted with CH2Cl2 and the CH2Cl2 layer was dried over MgSO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1) to afford 10 g of crude 1-isopropyl-6-(diethylaminosulfonyl)-4-chloro-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperaturewas refluxed for 6 hours
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialthe CH2Cl2 layer was dried over MgSO4
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1)

Sources & evidence

ORD record
ord-abcdcd05f048436ba9d0c875ffd779d4
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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