Hydrochloric Acid → 2,6-Dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1844166Notes

Reaction equation

HRID 1844166 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]([CH3:16])=[CH:6][N:5]2[C:17]=1[C:18]([O:20]CC)=[O:19].[OH-].[Li+].Cl>C1COCC1.CO>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]([CH3:16])=[CH:6][N:5]2[C:17]=1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86717929Ethyl 2,6-dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 867179302,6-Dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2.25 g (7.4 mmol) of ethyl 2,6-dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylate Example 88A were initially charged in 157 ml of THF/methanol (5:1), 37 ml (37 mmol) of 1N aqueous lithium hydroxide solution were added and the reaction mixture was stirred at RT over the weekend. The mixture was then cooled to 0° C., acidified to pH 4 with 6 N aqueous hydrochloric acid and freed from organic solvent on a rotary evaporator. The precipitated solid was filtered off, washed with water and dried under high vacuum. This gave 1.64 g (80% of theory; purity 100%) of the title compound.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. customfreed from organic solvent on a rotary evaporator
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-1d417fb9e0e1462e96124428f827e1d4
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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