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

HRID 1458755Notes

Reaction equation

HRID 1458755 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([O:18][CH3:19])=[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:24]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:24])=[C:6]2[CH:5]=[N:4]1)=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 19592240N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid

Product 1

HCID 195922121-ethyl-4-chloro-6-methoxy-1H-pyrazolo[3,4-b]quinoline

Procedure

A mixture of N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid (110 g, 0.421 mol) and POCl3 (300 ml) is refluxed overnight and then is allowed to stand at room temperature for about 3 days. The reaction mixture is poured into ice water and then is basified with NH4OH. The solid that forms is collected by filtration, washed with water and air dried to afford 100.5 g of 1-ethyl-4-chloro-6-methoxy-1H-pyrazolo[3,4-b]quinoline.

Workup

  1. temperatureis refluxed overnight
  2. filtrationThe solid that forms is collected by filtration
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-d8cb8f34d3e24a0c96e4c9c52f5a856c
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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