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

HRID 1586148Notes

Reaction equation

HRID 1586148 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([N+:18]([O-:20])=[O: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:25]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:25])=[C:6]2[CH:5]=[N:4]1)=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 21217728N-(1-ethylpyrazol-5-yl)-5-nitroanthranilic acid

Product 1

HCID 212177131-ethyl-4-chloro-6-nitro-1H-pyrazolo[3,4-b]quinolineYield 65%

Procedure

A mixture of N-(1-ethylpyrazol-5-yl)-5-nitroanthranilic acid (3.8 g, 13.77 mmol) and POCl3 (20 ml) is refluxed for 8 hours. The reaction mixture is poured into ice waterl, neutralized with concentrated NH4OH, and the resulting solid is collected by filtration, washed with water and dried to afford 2.5 g (65%) of 1-ethyl-4-chloro-6-nitro-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperatureis refluxed for 8 hours
  2. additionThe reaction mixture is poured into ice waterl
  3. filtrationthe resulting solid is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-95f36b1a90a440b0a40c370882d15704
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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