3-Methoxyaniline → HCID 22417859, compound

HRID 1720260Notes

Reaction equation

HRID 1720260 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[CH:14]=[N:13][NH:12][C:10]3=2)[N:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1>C(O)C>[ClH:1].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]4[CH:14]=[N:13][NH:12][C:10]4=3)[N:5]=[CH:4][CH:3]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 15290750HCID 15290750, compound

Product 1

HCID 22417859HCID 22417859, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 9-chloro-1H-pyrazolo[3,4-f]quinoline (1.10 g, 5.4 mmol) in absolute ethanol (50 ml) was added m-anisidine (0.79 ml, 7.1 mmol) and the reaction mixture heated at reflux for 48 hours. The solvent was removed by rotary evaporation and the residue was dissolved in boiling methanol, treated with decolorizing carbon and filtered to give a light yellow solution. The solvent was removed by rotary evaporation and the residue was recrystallized from methanol/ether to give 9-(m-anisidino)-1H-pyrazolo[3,4-f]quinoline hydrochloride (1.04 g, 59%) as off-white crystals.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 48 hours
  3. customThe solvent was removed by rotary evaporation
  4. dissolutionthe residue was dissolved
  5. additiontreated with decolorizing carbon
  6. filtrationfiltered
  7. customto give a light yellow solution
  8. customThe solvent was removed by rotary evaporation
  9. customthe residue was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-fbb994398bfd4bdbb7a8283cdcdbd248
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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