4-Ethoxyaniline → 7-(4-Ethoxyanilino)-5-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 637981Notes

Reaction equation

HRID 637981 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.[CH3:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1>>[CH2:13]([O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]3[CH:9]=[N:10][NH:11][C:3]=23)=[CH:19][CH:20]=1)[CH3:12]

Participants

3

Reactant 2

HCID 90764-EthoxyanilineHCID 116798717-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 202548577-(4-Ethoxyanilino)-5-methyl-1H-pyrazolo[4,3-b]pyridineYield 14%

Procedure

7-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (0.5 g, 0.003 mole) was heated at reflux temperature under nitrogen in p-phenetidine for 8 h. The mixture was left to stand at room temperature while a blue/black precipitate formed. This was collected, washed with water and ethyl acetate and the residue, a grey solid, was recrystallized from ethanol with charcoal present to give the required product as an off-white solid (0.11 g, 14%), m.p. 217° C.

Workup

  1. waitThe mixture was left
  2. customto stand at room temperature while a blue/black precipitate
  3. customformed
  4. customThis was collected
  5. washwashed with water and ethyl acetate
  6. customthe residue, a grey solid, was recrystallized from ethanol with charcoal present

Sources & evidence

ORD record
ord-dd4e7bdb32414c698fc5ad70d960b749
Source dataset
uspto-grants-1985_12
Patent number
US04559348

Reaction notes

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