Triethylamine → 2-Methylpyridine-4-carboxylic acid

HRID 732001Notes

Reaction equation

HRID 732001 reaction equation
[H][H].Cl[C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[C:6]([CH3:13])[N:5]=1.C(N(CC)CC)C>[Pd].C(O)C>[CH3:13][C:6]1[N:5]=[CH:4][CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 27628212-Methylpyridine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A hydrogen filled balloon was attached to a flask containing 2-chloro-6-methylpyridine-4-carboxylic acid (2 g, 12.0 mmol), palladium 10 wt. % on activated carbon (0.5 g), triethyl amine (4.8 ml) and ethanol (24 ml) and then stirred overnight at room temperature. The reaction mixture was filtered through celite, washed with methanol and concentrated. The residue was titurated with dichloromethane and then filtered to afford 6-methylpyridine-4-carboxylic acid as a white solid; 1.05 g (66%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with methanol
  3. concentrationconcentrated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-31468142018e4d9480df087a91535b50
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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