Lithium hydroxide, monohydrate → 6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid

HRID 402377Notes

Reaction equation

HRID 402377 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]([CH3:26])[N:17]=[N:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[N:9][CH:8]=1>O.C1COCC1.CO>[CH3:26][N:16]1[C:15]([CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:27])=[O:5])=[CH:8][N:9]=2)=[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:18]=[N:17]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 573346466-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 674982816-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acidYield 85.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (51 mg, 1.22 mmol) in water (1.5 mL) was added dropwise to a suspension of 6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid methyl ester (199 mg, 0.61 mmol) in THF (1.5 mL) and MeOH (0.3 mL). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was then evaporated and the residue dissolved in water, acidified with HCl (1N), and the resulting precipitate filtered off to afford the title product (162 mg, 70%) as a white solid. MS: m/e=310.3 [M−H]−.

Workup

  1. customThe reaction mixture was then evaporated
  2. dissolutionthe residue dissolved in water
  3. filtrationthe resulting precipitate filtered off

Sources & evidence

ORD record
ord-e1e67960bcb84ac8a8e046f6dfa085ea
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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