Methyl iodide → 6-(Methoxymethyl)pyridine-2-carboxylic acid

HRID 334053Notes

Reaction equation

HRID 334053 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH3:14]I>C1COCC1.CCOC(C)=O>[CH3:14][O:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117894046-(Hydroxymethyl)picolinic acid

Product 1

HCID 450826276-(Methoxymethyl)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 300 mg (1.96 mmol) 6-hydroxymethyl-pyridine-2-carboxylic acid in 20 mL THF was added 188 mg (4.31 mmol) NaH in mineral oil (55%) at 0° C. After gas formation ceased, 310 μL (4.90 mmol) methyl iodide was added dropwise, then the mixture was stirred for 1 h at 0° C. and for 1 h at RT. The reaction mixture was diluted with EtOAc, extracted with water, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo.

Workup

  1. extractionextracted with water
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6736bc0f0b3840618706e3de867459e5
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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