Hydrochloric Acid → 3-(5-Methylpyridin-2-yl)-5-(4-methyl-4H-1,2,4-triazol-3-yl)benzoic acid

HRID 888384Notes

Reaction equation

HRID 888384 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([C:18]3[N:22]([CH3:23])[CH:21]=[N:20][N:19]=3)[CH:17]=2)[C:11]([O:13]C)=[O:12])=[N:6][CH:7]=1.[OH-].[Li+].Cl>C1COCC1.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([C:18]3[N:22]([CH3:23])[CH:21]=[N:20][N:19]=3)[CH:17]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68498660Methyl 3-(5-methylpyridin-2-yl)-5-(4-methyl-4H-1,2,4-triazol-3-yl)benzoate

Product 1

HCID 684986543-(5-Methylpyridin-2-yl)-5-(4-methyl-4H-1,2,4-triazol-3-yl)benzoic acidYield 121.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(5-methylpyridin-2-yl)-5-(4-methyl-4H-1,2,4-triazol-3-yl)benzoate (0.37 g, 1.20 mmol) in THF (5 mL) was added lithium hydroxide (86 mg, 3.60 mmol) in 5 mL of water. After 16 h, the reaction was acidified to pH 1 by 1 M HCl. The solution was concentrated and dried under vacuum to give the hydrochloride salt of the title compound (0.43 g). MS 295.0 (M+1).

Workup

  1. concentrationThe solution was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-99954cd7651240f0a1f57e5815194a07
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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