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

HRID 1586163Notes

Reaction equation

HRID 1586163 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) is refluxed overnight. The reaction mixture is poured into ice water (400 ml), neutralized with NH4OH and extracted with CH2Cl2 (3×100 ml). The CH2Cl2 layers are combined and concentrated in vacuo, and the residue is 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. temperatureis refluxed overnight
  2. extractionextracted with CH2Cl2 (3×100 ml)
  3. concentrationconcentrated in vacuo
  4. customthe residue is purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-b670584ad1454a4a8e12c499a054afa6
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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