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

HRID 1586138Notes

Reaction equation

HRID 1586138 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:11]1[C:10]2[C:9](=[CH:17][CH:16]=[C:15]([O:18][CH3:19])[CH:14]=2)[N:8]=[C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=12

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 19592240N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid

Product 1

HCID 195922121-ethyl-4-chloro-6-methoxy-1H-pyrazolo[3,4-b]quinoline

Procedure

A mixture of N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid (27.5 g, 0.105 mol) and POCl3 (60 ml) is refluxed overnight. The reaction mixture is poured into ice waterl, basified with NH4OH and the solid which forms is collected by filtration to afford 20 g of 4-chloro-1-ethyl-6-methoxy-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperatureis refluxed overnight
  2. additionThe reaction mixture is poured into ice waterl
  3. filtrationthe solid which forms is collected by filtration

Sources & evidence

ORD record
ord-ce911e17de12486a8b5548ad7d69d6f0
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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