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

HRID 977147Notes

Reaction equation

HRID 977147 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]>>[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]([O:18][CH3:19])=[CH:16][CH:17]=3)[CH3:2]

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 (110 g, 0.421 mol) and POCl3 (300 mL) was refluxed overnight and then was allowed to stand at room temperature for about 3 days. The reaction mixture was poured into ice-water and then was basified with NH4OH. The solid which formed was collected by filtration, washed with water and air dried to afford 100.5 g of 1-ethyl-4-chloro-6-methoxy-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperaturewas refluxed overnight
  2. customThe solid which formed
  3. filtrationwas collected by filtration
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-55962809a30346a98dfa5d72f8e1181f
Source dataset
uspto-grants-1997_03
Patent number
US05614530

Reaction notes

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