Lithium Hydroxide → 6-[(Methylsulfonyl)methyl]nicotinic acid

HRID 14209Notes

Reaction equation

HRID 14209 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][N:7]=1)(=[O:4])=[O:3].[OH-].[Li+]>O1CCCC1.CO.O>[CH3:1][S:2]([CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21086215Methyl 6-((methylsulfonyl)methyl)nicotinate

Product 1

HCID 210859936-[(Methylsulfonyl)methyl]nicotinic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of methyl 6-[(methylsulfonyl)methyl]nicotinate (800 mg) in 1:1.1 tetrahydrofuran/methanol/water (30 mL) was added lithium hydroxide (440 mg). The mixture was stirred at room temperature for 1 h, and concentrated under reduced pressure. The residue was partitioned between water (10 mL) and chloroform (10 mL). The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid and extracted with 3:1 chloroform/2-propanol (3×30 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 700 mg of the title compound: 1H NMR (300 MHz, CD3OD) δ 9.07, 8.33, 7.65, 4.77, 3.06.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water (10 mL) and chloroform (10 mL)
  3. extractionextracted with 3:1 chloroform/2-propanol (3×30 mL)
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db09fd88effa429fbf0b48b9d469ad24
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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