Sodium Hydroxide → Imidazo[1,2-a]pyridin-2-ylmethanamine

HRID 983357Notes

Reaction equation

HRID 983357 reaction equation
[N:1]1[C:2]([CH2:10][N:11]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[OH-].[Na+]>O.NN.C(O)C>[N:1]1[C:2]([CH2:10][NH2:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 225596052-(imidazo[1,2-a]pyridin-2-ylmethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 2771121Imidazo[1,2-a]pyridin-2-ylmethanamineYield 58.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

A solution of 1.37 g (4.94 mmol) of 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-1H-isoindole-1,3(2H)-dione in 14 ml of hydrazine hydrate 98% and 1 ml of ethanol. Was stirred at room temperature for an hour. The mixture was then poured into 25 ml of sodium hydroxide 35% and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and evaporated to give 0.426 g of the title compound crystallized from diethylether.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-58488a4e8db943eaad2ad45aa43cbc5b
Source dataset
uspto-grants-2005_03
Patent number
US06863647B2

Reaction notes

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