Ammonium Hydroxide → 1-ethyl-4-chloro-7-methoxy-1H-pyrazolo[3,4-b]quinoline
Reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][CH:15]=[C:16]([O:18][CH3:19])[CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].O=P(Cl)(Cl)[Cl:22].[NH4+].[OH-]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:22])=[C:6]2[CH:5]=[N:4]1)=[CH:14][CH:15]=[C:16]([O:18][CH3:19])[CH:17]=3)[CH3:2]Participants
4
Procedure
A mixture of N-(1-ethylpyrazol-5-yl)-4-methoxyanthranilic acid (13.3 g, 0.051 mol) and POCl3 (125 ml) was refluxed for 3 hours, then was allowed to sit overnight. The volume of POCl3 was reduced, then ice/water, followed by NH4OH was added. A precipitate formed which was collected by filtration and dried in a vacuum oven at 50° C. to afford 11.51 g (87%) of 1-ethyl-4-chloro-7-methoxy-1H-pyrazolo[3,4-b]quinoline, m.p. 95-98° C.