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

HRID 1586132Notes

Reaction equation

HRID 1586132 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]>>[Cl:23][C:11]1[C:10]2[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=[C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([CH3:18])[C:6]=12

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 (210 ml) is refluxed for 24 hours. The reaction mixture is cooled to room temperature, poured into ice waterl and neutralized with concentrated NH4OH to a pH of 8.0. The product which slowly crystallized from the solution is collected by filtration, washed with water and dried to afford 6.7 g (95%) of 4-chloro-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperatureis refluxed for 24 hours
  2. customThe product which slowly crystallized from the solution
  3. filtrationis collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2b51d6c6069a4a11b4d78102b68606bb
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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