Sodium Hydroxide → 7-Methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 130667Notes

Reaction equation

HRID 130667 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:13]([O:15]CC)=[O:14])=[C:10]([CH3:12])[N:11]=[C:5]2[CH:4]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:13]([OH:15])=[O:14])=[C:10]([CH3:12])[N:11]=[C:5]2[CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 53485249Ethyl 7-methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 534853377-Methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-methoxy-2-methylimidazo[1,2-α]pyridine-3-carboxylate (1.8 g, 7.7 mmol) in THF (100 ml) and MeOH (50 ml) was added aq. NaOH (11.5 ml, 2M, 23.1 mmol) and the resulting emulsion heated to reflux for 2 hours. A further aliquot of NaOH was then added (3.8 ml, 2M, 7.7 mmol) and the resulting mixture heated for a further 2 hours. The solvents were removed in-vacuo and the residue was acidified with 1.5 N HCl to pH 3, and the resulting solid was filtered off, washed with water and dried in vacuo to yield 7-methoxy-2-methylimidazo[1,2-α]pyridine-3-carboxylic acid, 1.2 g, 76%, as an off white solid.

Workup

  1. temperaturethe resulting emulsion heated
  2. temperatureto reflux for 2 hours
  3. temperaturethe resulting mixture heated for a further 2 hours
  4. customThe solvents were removed in-vacuo
  5. filtrationthe resulting solid was filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5a8bf282ec0e4570a0f8649c0b547d30
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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