Lithium Hydroxide → HCID 55265823, compound

HRID 706746Notes

Reaction equation

HRID 706746 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]([O:14]CC)=[O:13])=[CH:10][N:11]=[C:5]2[CH:4]=1)#[N:2].[Li+].[OH-]>C1COCC1.CCO.O>[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]([OH:14])=[O:13])=[CH:10][N:11]=[C:5]2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67976057HCID 67976057, compound

Product 1

HCID 55265823HCID 55265823, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a mixture of ethyl 7-cyanoimidazo[1,2-a]pyridine-3-carboxylate (2.23 g, 10.4 mmol) in 100 mL of THF:EtOH:water (1:2:1) was added LiOH (0.248 g, 10.4 mmol). The reaction mixture was stirred at ambient temperature overnight. The reaction was concentrated and diluted with water, cooled in an ice bath and acidified to pH=3 with 1 M HCl producing a white precipitate. The precipitate was removed by vacuum filtration and dried under vacuum with a methanol azeotrope providing 1.62 g of the title compound as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. temperaturecooled in an ice bath
  4. customThe precipitate was removed by vacuum filtration
  5. dry with materialdried under vacuum with a methanol

Sources & evidence

ORD record
ord-6ff7d48d06b34053b4d96f2c1568d839
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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