Ammonium formate → 2-Methylpyridine-3-carbonitrile

HRID 2360599Notes

Reaction equation

HRID 2360599 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[N:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:10][C:4]1[N:3]=[CH:2][CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 123877376-Chloro-2-methylnicotinonitrile

Product 1

HCID 47383082-Methylpyridine-3-carbonitrileYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-Chloro-2-methylnicotinonitrile (132, 10 g, 66 mmol) and ammonium formate (41 g, 0.65 mol) were dissolved in methanol (250 mL), and palladium (5% on activated carbon, 3.5 g, 2.5 mol %) was added. The mixture was stirred at room temperature for 12 h, filtered through Celite, and washed with methanol (3×50 mL). The combined filtrates were evaporated, and the yellow oily residue was subjected to flash column chromatography on silica gel, eluting with chloroform to provide 133 as an off-white solid (6.3 g, 81%): mp 55° C. (lit. (J. Med. Chem. 2000, 43, 3168-3185) mp 56-58° C.). 1H NMR (300 MHz, CDCl3) δ 7.80 (dd, J=4.9, 1.6 Hz, 1H), 7.02 (dd, J=7.8, 1.7 Hz, 1H), 6.37 (dd, J=7.8, 5.0 Hz, 1H), 1.88 (s, 3H); positive ion ESIMS m/z (rel intensity): 119 (MH+, 100).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with methanol (3×50 mL)
  3. customThe combined filtrates were evaporated
  4. washeluting with chloroform

Sources & evidence

ORD record
ord-88fe82ec4d3344c685132211f037fce6
Source dataset
uspto-grants-2014_04
Patent number
US08686146B2

Reaction notes

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