Potassium Hydroxide → 1-Ethyl-4-[[2-(ethylamino)phenyl]amino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 596760Notes

Reaction equation

HRID 596760 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:24][CH2:25][CH3:26])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])C.[OH-].[K+]>>[CH3:26][CH2:25][NH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]2[N:12]([CH2:15][CH3:16])[N:13]=[CH:14][C:8]=12

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 54081216HCID 54081216, compound

Product 1

HCID 214481641-Ethyl-4-[[2-(ethylamino)phenyl]amino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Procedure

3.5 g. of 4-[[(2-ethylamino)phenyl]amino]-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.01 mol.) are heated at 60° for 12 hours with a solution of 1.7 g. of potassium hydroxide in 50 ml. of alcohol. The solvent is distilled off and the residue is dissolved in about 100 ml. of water. On acidifying with acetic acid, 4-[[(2-ethylamino)phenyl]amino]-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid crystallizes and is purified by recrystallization from acetic acid, yeild 2.8 g. (93%), m.p. 224°-226°.

Workup

  1. distillationThe solvent is distilled off
  2. dissolutionthe residue is dissolved in about 100 ml
  3. customcrystallizes
  4. customis purified by recrystallization from acetic acid, yeild 2.8 g

Sources & evidence

ORD record
ord-8302673396ce4f65b58954296ff46aff
Source dataset
uspto-grants-1977_03
Patent number
US04012373

Reaction notes

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