Triethylamine → 2-Methylpyridine-4-carboxylic acid

HRID 273088

Reaction equation

HRID 273088 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 is 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%). 1H NMR (MeOD) δ (ppm): 8.62 (d, 1H), 7.68 (s, 1H), 7.60 (d, 1H), 2.55 (s, 3H).

Workup

  1. customThe is reaction mixture
  2. filtrationwas filtered through celite
  3. washwashed with methanol
  4. concentrationconcentrated
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3db16f75d17b4f68b39d141a45c58893
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Linked notes

Loading…