Pyridine → 6-Isobutyl-5-methylnicotinonitrile

HRID 2065894Notes

Reaction equation

HRID 2065894 reaction equation
[CH2:1]([C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]([NH2:11])=O)=[CH:7][N:6]=1)[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]#[N:11])=[CH:7][N:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 1049PyridineHCID 670268976-Isobutyl-5-methylnicotinamide

Product 1

HCID 670269756-Isobutyl-5-methylnicotinonitrileYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-isobutyl-5-methyl-nicotinamide (1.89 g, 9.85 mmol) in DCM (40 mL) and pyridine (2.83 g, 39.4 mmol), TFA anhydride (5.17 g, 24.6 mmol) is added portionwise at 0° C. The mixture is stirred at rt for 24 h, diluted with DCM and washed with water, 4% aq. citric acid solution followed by sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 6-isobutyl-5-methyl-nicotinonitrile (1.35 g) as a white solid; LC-MS: tR=0.89 min, [M+1]+=175.11.

Workup

  1. washwashed with water, 4% aq. citric acid solution
  2. extractionextract
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-ed548ffc34534ec9930bf45ed8a362cf
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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