Ammonium Hydroxide → 1-ethyl-4-chloro-7-methoxy-1H-pyrazolo[3,4-b]quinoline

HRID 613272Notes

Reaction equation

HRID 613272 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

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychloride2×HCID 19592233N-(1-ethylpyrazol-5-yl)-4-methoxyanthranilic acid

Product 1

HCID 195922181-ethyl-4-chloro-7-methoxy-1H-pyrazolo[3,4-b]quinolineYield 87%

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.

Workup

  1. temperaturewas refluxed for 3 hours
  2. additionwas added
  3. customA precipitate formed which
  4. filtrationwas collected by filtration
  5. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-fc02dee562ac4fc18052c5e042e1eb35
Source dataset
uspto-grants-1999_12
Patent number
US06008226

Reaction notes

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