Lithium Hydroxide → 2-(4-Methylsulfanyl-phenoxy)-nicotinic acid

HRID 724279

Reaction equation

HRID 724279 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1.[OH-].[Li+]>O1CCCC1>[CH3:18][S:17][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:19])=[O:2])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 587461792-(4-Methylsulfanyl-phenoxy)-nicotinic acid methyl ester

Product 1

HCID 218771372-(4-Methylsulfanyl-phenoxy)-nicotinic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-methylsulfanyl-phenoxy)-nicotinic acid methyl ester (10.36 g, 37.6 mmol) was dissolved in tetrahydrofuran (140 ml) and 1M aqueous lithium hydroxide solution (94 ml, 94 mmol) was added. The reaction was stirred at room temperature for 18 h and the tetrahydrofuran was removed under reduced pressure. The residue was acidified to pH1 with concentrated hydrochloric acid and the resulting precipitate was filtered, washed with water (2×10 ml), diethyether (3×10 ml) and dried in vacuo to give 2-(4-methylsulfanyl-phenoxy)-nicotinic acid (9.3 g) as a white solid.

Workup

  1. customthe tetrahydrofuran was removed under reduced pressure
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water (2×10 ml), diethyether (3×10 ml)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b6cd68847df546618176856ee718bfc1
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Linked notes

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