Ammonium Hydroxide → 1-ethyl-4-chloro-6-acetamido-1H-pyrazolo[3,4-b]quinoline

HRID 375879Notes

Reaction equation

HRID 375879 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].O=P(Cl)(Cl)[Cl:24].[NH4+].[OH-]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:24])=[C:6]2[CH:5]=[N:4]1)=[CH:14][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:16][CH:17]=3)[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 21217715N-(1-ethylpyrazole-5-yl)-5-acetamidoanthranilic acid

Product 1

HCID 212176891-ethyl-4-chloro-6-acetamido-1H-pyrazolo[3,4-b]quinoline

Procedure

A mixture of N-(1-ethylpyrazole-5-yl)-5-acetamido anthranilic acid (2 g) and POCl3 (20 ml) was refluxed overnight. The reaction mixture was poured into ice-water (400 ml), neutralized with NH4OH and extracted with CH2Cl2 (3×100 ml). The CH2Cl2 layers were combined and concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford 0.2 g of 1-ethyl-4-chloro-6-acetamido-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with CH2Cl2 (3×100 ml)
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-3febb04eb6cc4aa28d8202dbf15c2102
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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