Lithium hydroxide, monohydrate → 4-Fluoro-3-(imidazo[1,2-a]pyridine-3-carboxamido)benzoic Acid

HRID 335335Notes

Reaction equation

HRID 335335 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]2=[N:17][CH:16]=1)=[O:14].O.[OH-].[Li+]>O.C1COCC1.CO>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]2=[N:17][CH:16]=1)=[O:14]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71282942HCID 71282942, compound

Product 1

HCID 712829884-Fluoro-3-(imidazo[1,2-a]pyridine-3-carboxamido)benzoic Acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl 4-fluoro-3-(imidazo[1,2-a]pyridine-3-carboxamido)benzoate (step 1) (7.2 g, 22.98 mmol) in water (30 ml), THF (45.0 ml) and MeOH (15.00 ml) was treated with lithium hydroxide monohydrate (4.82 g, 115 mmol). The reaction mixture was stirred at RT overnight and concentrated in vacuo to remove THF and MeOH. The resulting mixture was acidified with 2M HCl to yield a solid that was collected by filtration and washed with ether (3×). The white solid was dried in the vacuum oven at 50° C. to afford the title compound as a hydrochloride salt;

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove THF and MeOH
  3. customto yield a solid
  4. filtrationthat was collected by filtration
  5. washwashed with ether (3×)
  6. customThe white solid was dried in the vacuum oven at 50° C.

Sources & evidence

ORD record
ord-b468726cf9c34361bef14a6865825417
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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