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

HRID 375859Notes

Reaction equation

HRID 375859 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) was heated on a steam bath overnight. The reaction mixture was poured into ice-water, neutralized with NH4OH and the precipitate which formed was 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. temperaturewas heated on a steam bath overnight
  2. customthe precipitate which formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c7b057d16807467c9c5f22f6b70712d8
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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