Sodium Hydroxide → 4-Butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 1576093Notes

Reaction equation

HRID 1576093 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:16]([NH:15][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]2[NH:12][N:13]=[CH:14][C:8]=12)[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 537827204-butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 215143004-Butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.6 of 4-butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.01 mol) is treated with 1.1 g of sodium hydroxide in 30 ml of ethanol for 20 hours at room temperature. The solvent is removed in vacuo and the residue is dissolved in 10 ml of water. On acidification with acetic acid 4-butylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid solidifies and is filtered off. The product is purified by recrystallization from acetic acid, yield 1.9 g (82%), m.p. 225°.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in 10 ml of water
  3. filtrationis filtered off
  4. customThe product is purified by recrystallization from acetic acid, yield 1.9 g (82%), m.p. 225°

Sources & evidence

ORD record
ord-6150b1dd3933405e8e9670a9972b1333
Source dataset
uspto-grants-1976_09
Patent number
US03979399

Reaction notes

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