Hydrochloric Acid → 3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carboxylic Acid

HRID 34108Notes

Reaction equation

HRID 34108 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=C(C#N)[CH:9]=2)[N:4]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[OH-:32].[Li+].Cl.[CH2:35]([OH:37])[CH3:36]>>[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:36]([C:35]([OH:32])=[O:37])[CH:9]=2)[N:4]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 689267013-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carbonitrile

Product 1

HCID 689282723-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carboxylic Acid

Procedure

To a suspension of 3.0 g of 3-iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carbonitrile obtained by Production example 431 in 20 mL of ethanol was added 20 mL of 4N lithium hydroxide aqueous solution at room temperature, and heated at reflux for a day. After cooling to room temperature, the solution was neutralized with 5N hydrochloric acid aqueous solution, and the precipitated crystals were collected by filtration. The crystals were washed successively with water and diethyl ether, to afford 3.0 g of the title compound as colorless crystals.

Workup

  1. temperatureheated
  2. temperatureat reflux for a day
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThe crystals were washed successively with water and diethyl ether

Sources & evidence

ORD record
ord-3e1de7d11efd4455901368ce68d996d1
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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