Hydrochloric Acid → 8-(Benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1844115Notes

Reaction equation

HRID 1844115 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[C:12]2[N:13]([C:17]([C:21]([O:23]CC)=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:14]=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>O1CCOCC1>[CH2:3]([O:10][C:11]1[C:12]2[N:13]([C:17]([C:21]([OH:23])=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:14]=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 44382335Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-A]pyridine-3-carboxylate

Product 1

HCID 98822068-(Benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

253 ml of 2N aqueous sodium hydroxide solution were added to a solution of 15.7 g (50.59 mmol) of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate in 253 ml of dioxane, and the mixture was stirred at room temperature for 14 hours. 101 ml of 6N hydrochloric acid were then added to the mixture. The solid formed was filtered off, washed with water and with methyl tert-butyl ether and then dried in a vacuum drying cabinet at 40° C. overnight. This gave 15.49 g (108% of theory) of 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid as a colourless solid. The yield was more than 100% owing to water of crystallization (1H NMR).

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed with water and with methyl tert-butyl ether
  4. customdried in a vacuum
  5. customdrying cabinet at 40° C. overnight
  6. customThe yield was more than 100% owing to water of crystallization (1H NMR)

Sources & evidence

ORD record
ord-34027cc8c8f245749cb172b97ae53f1c
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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