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

HRID 2275781Notes

Reaction equation

HRID 2275781 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 acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

253 ml of 2 N aqueous sodium hydroxide solution were added to a solution of 15.7 g of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate (50.59 mmol) in 253 ml of 1,4-dioxane, and the mixture was stirred at RT for 14 h. 101 ml of 6 N aqueous hydrochloric acid were then added. The solid formed was filtered off, washed with water and methyl tert-butyl ether and then dried under reduced pressure at 40° C. overnight. This gave 15.49 g (108% of theory) of 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid.

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed with water and methyl tert-butyl ether
  4. customdried under reduced pressure at 40° C. overnight

Sources & evidence

ORD record
ord-09567556c5b545d287405ad8ee3610f3
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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