Sodium Hydroxide → (2-Methylpyrazolo[1,5-a]pyridin-4-yl)methanol

HRID 1639743Notes

Reaction equation

HRID 1639743 reaction equation
[OH:1][CH2:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([CH3:17])[C:11]=2C(OCC)=O)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:17][C:10]1[CH:11]=[C:4]2[C:3]([CH2:2][OH:1])=[CH:8][CH:7]=[CH:6][N:5]2[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59334472Ethyl 4-(hydroxymethyl)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 59334539(2-Methylpyrazolo[1,5-a]pyridin-4-yl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 4-(hydroxymethyl)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylate (41.0 g, 0.180 mol) and 40% aqueous sulfuric acid solution (350 mL) was stirred at 100° C. for 2 hr. The reaction mixture was basified with 10% aqueous sodium hydroxide solution, and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (28.0 g, yield 99%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-34668994e19f439cace307091e02eaa3
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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