Lithium Hydroxide → 5-Amino-6-chloroimidazo[1,2-a]pyridine-8-carboxylic acid

HRID 965790Notes

Reaction equation

HRID 965790 reaction equation
[NH2:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([C:11]([O:13]CC)=[O:12])=[CH:4][C:3]=1[Cl:16].[OH-].[Li+]>CO>[NH2:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[Cl:16]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 12088090Ethyl 5-amino-6-chloroimidazo[1,2-a]pyridine-8-carboxylate

Product 1

HCID 120880915-Amino-6-chloroimidazo[1,2-a]pyridine-8-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 5-amino-6-chloroimidazo[1,2-a]pyridine-8-carboxylate (Example 1, METHOD A, Step 3, 217 mg, 0.91 mmol) in methanol (5 mL) was added 1N aqueous lithium hydroxide (500 μL) and the mixture was stirred overnight at room temperature. The solvent was removed in vacuo and acidified with 1N hydrochloric acid. The resultant precipitate was collected by filtration to give 165 mg (86%) of the title compound as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-6f4e84dcb75f4f718cab610a33144212
Source dataset
uspto-grants-2005_10
Patent number
US06951867B2

Reaction notes

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