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

HRID 1586183Notes

Reaction equation

HRID 1586183 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) is refluxed for 6 hours. The reaction mixture is cooled to room temperature, and then is poured into ice water and neutralized with concentrated NH4OH. The mixture is extracted with CH2Cl2 and the CH2Cl2 layer is dried over MgSO4 and evaporated to dryness. The residue is 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. temperatureis refluxed for 6 hours
  2. extractionThe mixture is extracted with CH2Cl2
  3. dry with materialthe CH2Cl2 layer is dried over MgSO4
  4. customevaporated to dryness
  5. customThe residue is purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1)

Sources & evidence

ORD record
ord-0c22364d26d84e989f405afbfaf1261c
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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