5-Methylnicotinic acid → (5-Methylpyridin-3-yl)methanol

HRID 1784934Notes

Reaction equation

HRID 1784934 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].FC1C=C(C(O)=O)C=C(C=1)C(O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 2562085-Methylnicotinic acidHCID 3273955-Fluoroisophthalic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11962777(5-Methylpyridin-3-yl)methanolYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To stirring solution of 233 mg (1.70 mmol) of 5-methylnicotinic acid (synthesized following the general procedure for 5-fluoro-isophthalic acid) in 30 mL of THF at 0° C. was added 181 mg (4.76 mmol) of LiAlH4. After 25 min., the reaction was quenched by adding successively 180 μL of H2O, 180 μL of 15% aqueous NaOH, and 540 μL of brine. The mixture was filtered through Celite and concentrated to give 87 mg of crude (5-methylpyridin-3-yl)methanol which was used for the next reaction without further purification.

Workup

  1. customsynthesized
  2. customat 0° C.
  3. customthe reaction was quenched
  4. additionby adding successively 180 μL of H2O, 180 μL of 15% aqueous NaOH, and 540 μL of brine
  5. filtrationThe mixture was filtered through Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c5b51a862e25494ea7c5e2e8520f0ea2
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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