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

HRID 1456026Notes

Reaction equation

HRID 1456026 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][C:5]([CH3:18])=[N:4]1)[CH3:2].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:23])=[C:6]2[C:5]([CH3:18])=[N:4]1)=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 19592214HCID 19592214, compound

Product 1

HCID 195922341-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinolineYield 95%

Procedure

A mixture of N-(1-ethyl-3-methylpyrazol-5-yl)anthranilic acid (7.0 g, 28.57 mmol) and POCl3 (20 ml) was refluxed for 24 hours. The reaction mixture was cooled to room temperature and then was poured into ice-water. The mixture was neutralized with concentrated NH4OH to a pH of about 8 and the resulting gum crystallized slowly to afford a solid which was collected by filtration, washed with water and dried to afford 6.7 g (95%) of 1-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customthe resulting gum crystallized slowly
  3. customto afford a solid which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d380a0fd8454468c9dc95b4bc9e3f708
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

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