Sodium Hydroxide → 8-Methyl-2-propylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 326675Notes

Reaction equation

HRID 326675 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]2[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][N:7]2[C:13]=1[C:14]([O:16]CC)=[O:15])[CH2:2][CH3:3].[OH-].[Na+]>C(O)C>[CH2:1]([C:4]1[N:5]=[C:6]2[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][N:7]2[C:13]=1[C:14]([OH:16])=[O:15])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 197356202-n-Propyl-3-ethoxycarbonyl-8-methylimidazo[1,2-a]pyridine

Product 1

HCID 197357648-Methyl-2-propylimidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21.0 g (86 mMol) of 2-n-propyl-3-ethoxycarbonyl-8-methylimidazo[1,2-a]pyridine are dissolved in 200 ml of ethanol, mixed with 100 ml of 2N sodium hydroxide solution and stirred for 4 days at ambient temperature. The solvent is evaporated off in vacuo at 40° C., the residue is diluted with water and combined with 20 g of ammonium chloride. The pH is adjusted to 6.5 by the addition of glacial acetic acid. After 2 hours, the precipitate formed is suction filtered, washed with water and dried in vacuo at 40° C.

Workup

  1. customThe solvent is evaporated off in vacuo at 40° C.
  2. additionthe residue is diluted with water
  3. additionThe pH is adjusted to 6.5 by the addition of glacial acetic acid
  4. waitAfter 2 hours
  5. customthe precipitate formed
  6. filtrationfiltered
  7. washwashed with water
  8. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-cd850eb6334e4d5db15deb9064ea91c6
Source dataset
uspto-grants-1993_12
Patent number
US05270322

Reaction notes

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