6-Methylpyridine-2-carboxylic acid → HCID 3815667, compound

HRID 1791358Notes

Reaction equation

HRID 1791358 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1>C(O)C.O.[Pt](=O)=O>[CH3:1][CH:2]1[NH:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 702826-Methylpyridine-2-carboxylic acid

Product 1

HCID 3815667HCID 3815667, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6-Methyl-pyridine-2-carboxylic acid (4.11 g, 30 mmol) was mixed with platinum(IV) oxide (35 mg, 0.154 mmol) in ethanol (50 mL) and water (25 mL) and stirred under hydrogen for 3 days. The reaction mixture was filtered through the celite and concentrated to dry. The residue was triturated with diethyl ether to give 4.1 g (98.3%) of the title compound as a white solid. 1H NMR (CDCl3), δ(ppm): 3.39 (dd,1H), 3.11 (m, 1H), 2.28 (d, 1H), 1.88 (m, 2H), 1.35–1.67 (m, 3H), 1.32 (d, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through the celite and
  2. concentrationconcentrated
  3. customto dry
  4. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-cd10f91b73694d80bba3c4a92731a1f1
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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