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

HRID 375854Notes

Reaction equation

HRID 375854 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) was refluxed overnight. The reaction mixture was poured into ice-water, basified with NH4OH and the solid which formed was collected by filtration to afford 20 g of 4-chloro-1-ethyl-6-methoxy-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperaturewas refluxed overnight
  2. customthe solid which formed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7635fe0296304b05aad2ff529bb07724
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

Loading…