Lithium hydroxide, monohydrate → Lithium 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

HRID 706610Notes

Reaction equation

HRID 706610 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O:14]CC)=[O:13])=[CH:10][N:11]=2)[CH:8]=1)#[N:2].O.[OH-].[Li+:19]>O1CCCC1.C(O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[CH:8]=1)#[N:2].[Li+:19]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67259960Ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 67260216Lithium 6-cyanoimidazo[1,2-a]pyridine-3-carboxylateYield 100.4%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

Ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate (13.9 g, 65 mmol) and lithium hydroxide monohydrate (2.7 g, 65 mmol) were dissolved in tetrahydrofuran/ethanol/water (1:2:1, 150 mL:300 mL:150 mL). After stirring for 16 hours at ambient temperature, the solvent was removed under vacuum to give lithium 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate (12.6 g).

Workup

  1. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-9f4dec8022ae4da4ad315548848cb30f
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…