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

HRID 375848Notes

Reaction equation

HRID 375848 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) was refluxed for 24 hours. The reaction mixture was cooled to room temperature, poured into ice-water and neutralized with concentrated NH4OH to a pH of 8.0. The product which slowly crystallized from the solution was 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. temperaturewas refluxed for 24 hours
  2. customThe product which slowly crystallized from the solution
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6200b5fb9d6f43bcb023ffcc03f6d07c
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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