Sodium Hydroxide → HCID 178433897, compound

HRID 497950Notes

Reaction equation

HRID 497950 reaction equation
[OH:1][C:2]1[C:7](C(O)=O)=[CH:6][N:5]=[C:4]2[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[C:13]([CH3:14])[C:3]=12.[OH-].[Na+]>P(=O)(O)(O)O>[CH3:14][C:13]1[C:3]2[C:2]([OH:1])=[CH:7][CH:6]=[N:5][C:4]=2[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178433901HCID 178433901, compound

Product 1

HCID 178433897HCID 178433897, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 4-hydroxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (2.0 g, 6.7 mmol) in phosphoric acid (10 mL) was heated and stirred at 180° C. for 12 hours. The reaction solution was cooled to room temperature, neutralized by the addition of an aqueous sodium hydroxide solution, and organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Purification of the residue by silica gel column chromatography (chloroform:methanol=95:5) gave the title compound (230 mg, 15% yield).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionwas extracted with chloroform
  4. washThe extract was washed with saturated brine and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customPurification of the residue by silica gel column chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-6c8cf89897c141e495cb6985d2680b0e
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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