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

HRID 2092618Notes

Reaction equation

HRID 2092618 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-20b88bf15c3147499984d9a22868d102
Source dataset
uspto-grants-2013_05
Patent number
US08440708B2

Reaction notes

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