Lithium hydroxide, monohydrate → HCID 178524732, compound

HRID 706667Notes

Reaction equation

HRID 706667 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O-:13])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.O.[OH-].[Li+]>C1COCC1.C(O)C.O>[OH:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 178524731HCID 178524731, compound

Product 1

HCID 178524732HCID 178524732, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

A solution of 7-hydroxyimidazo[1,2-a]pyridine-3-carboxylate (414 mg, 2.01 mmol) in a 2:1:1 THF/ethanol/water mixture (36 mL) was treated at ambient temperature with lithium hydroxide monohydrate (2.1 equivalents). The reaction mixture was stirred at ambient temperature overnight. To the reaction were then added another 2.1 equivalents of lithium hydroxide monohydrate and stirring continued for 72 hours. After removal of the volatiles the mixture was diluted with water, cooled in an ice bath, and the pH adjusted to 4 with aqueous 6N hydrochloric acid. The resulting white precipitate was isolated and dried to afford the desired product (358 mg).

Workup

  1. stirringstirring
  2. waitcontinued for 72 hours
  3. customAfter removal of the volatiles the mixture
  4. additionwas diluted with water
  5. temperaturecooled in an ice bath
  6. customThe resulting white precipitate was isolated
  7. customdried

Sources & evidence

ORD record
ord-32c99e349bc740d18d20737c68b96ef0
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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