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

HRID 2266738Notes

Reaction equation

HRID 2266738 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 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH hydrate (82 mg, 1.94 mmol) in H2O (7 mL) was added dropwise to a suspension of 3-iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (526 mg, 1.49 mmol) in THF (4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred until the reaction solution turned into 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 (470 mg, 93%). MS (M+H)=340.

Workup

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

Sources & evidence

ORD record
ord-fa3757f2fdb44c5cad3fe48b03acf66d
Source dataset
uspto-grants-2010_12
Patent number
US07858654B2

Reaction notes

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