Citric Acid → HCID 71280499, compound

HRID 405815Notes

Reaction equation

HRID 405815 reaction equation
[O:1]=[C:2]([CH3:17])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([O-:16])=[O:15])=[CH:12][N:13]=2)[CH:10]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[O:1]=[C:2]([CH3:17])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 86677453HCID 86677453, compound

Product 1

HCID 71280499HCID 71280499, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A stirring mixture of ethyl 6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylate (77) (190 mg, 0.730 mmol) and 2N LiOH (0.2 mL) in THF:MeOH (4:1, 3 mL) was heated at 50° C. for 45 minutes. The reaction was cooled to room temperature and the pH was adjusted between 3-5 with 10% citric acid. The solvent was partially reduced. The resulting solid was collected by vacuum filtration and washed with excess water. Crude 6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid (78) was dried and used in the next step without further purification. MS m/z 233.08 (M+1)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. washwashed with excess water
  4. dry with materialCrude 6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid (78) was dried
  5. customused in the next step without further purification

Sources & evidence

ORD record
ord-ba31aa6a94d14a6cb476faeafe4ef5d7
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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