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

HRID 1586143Notes

Reaction equation

HRID 1586143 reaction equation
[C:1]1([CH2:7][N:8]2[C:12]([NH:13][C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16](O)=O)=[CH:11][CH:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH4+].[OH-].O=P(Cl)(Cl)[Cl:27]>>[C:1]1([CH2:7][N:8]2[C:12]3=[N:13][C:14]4[C:15]([C:16]([Cl:27])=[C:11]3[CH:10]=[N:9]2)=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 54572611N-(1-phenylmethylpyrazol-5-yl) anthranilic acid

Product 1

HCID 212176971-phenylmethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Procedure

A mixture of N-(1-phenylmethylpyrazol-5-yl) anthranilic acid (6 g) and POCl3 (60 ml) is heated on a steam bath overnight. The reaction mixture is poured into ice waterl, neutralized with NH4OH, and the precipitate which forms is collected by filtration,washed with water and dried to afford 5 g of 1-phenylmethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline, as a light brown powder.

Workup

  1. temperatureis heated on a steam bath overnight
  2. additionThe reaction mixture is poured into ice waterl
  3. filtrationthe precipitate which forms is collected by filtration,washed with water
  4. customdried

Sources & evidence

ORD record
ord-2431f59fcb3a4ccda394aeb4224af4da
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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