Lithium hydroxide, monohydrate → 3-Iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid

HRID 1888923Notes

Reaction equation

HRID 1888923 reaction equation
O[Li].O.C[O:5][C:6](=[O:21])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:10]=[C:9]([I:20])[CH:8]=1>O.C1COCC1>[I:20][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:10]=1)[C:6]([OH:21])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 594325793-Iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Product 1

HCID 595997013-Iodo-5-(5-methyl-pyridin-2-yl)-benzoic acidYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH hydrate (20 mg) in H2O (5 mL) was added dropwise to a suspension of 3-iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (85 mg, 0.2 mmol) in THF (1 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred until the reaction solution turned clear. Solvent was removed under vacuum and the resulting aqueous solution was acidified by 10% HCl to pH=6-7. The resulting precipitate was collected and dried to afford 3-iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid (68 mg, 95%), MS (M+H)=339.

Workup

  1. customSolvent was removed under vacuum
  2. customThe resulting precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-3b9d1f61ce024f27ba3e403d64cb0f0d
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

Loading…