5-Ethynylnicotinonitrile → 5-Ethylnicotinonitrile

HRID 1720901Notes

Reaction equation

HRID 1720901 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([C:9]#[CH:10])[CH:8]=1)#[N:2]>O1CCCC1.[C].[Pd]>[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH2:9][CH3:10])[CH:8]=1)#[N:2]

Participants

4

Reactant 1

HCID 224165635-Ethynylnicotinonitrile

Product 1

HCID 53252845-EthylnicotinonitrileYield 84.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Cyano-5-ethynylpyridine (1 g) was dissolved in tetrahydrofuran (30 ml) and subjected to catalytic hydrogenation under hydrogen stream in the presence of 10% palladium-carbon (100 mg) as a catalyst. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure to give 0.87 g of 3-cyano-5-ethylpyridine (yield, 84%). 1H-NMR (90 MHz, CDCl3): δ (ppm) 8.58(1H, H-2), 8.39(1H, H-6), 7.77(1H, H-4), 2.72(2H, q, J=7.5Hz, Pyridine-CH2CH3), 1.26(3H, t, J=7.5Hz, Pyridine-CH2CH3).

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8bab8b716ce24bccb14adc344ac3f005
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

Loading…