Benzonitrile → 3-Amino-5-(tert-butyl)-2-methoxybenzonitrile

HRID 735800Notes

Reaction equation

HRID 735800 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([O-:11])=O.[NH4+:12]>C(OCC)(=O)C.CO.[Pd]>[NH2:12][C:4]1[C:3]([O:11][CH3:9])=[C:2]([CH:7]=[C:6]([C:2]([CH3:7])([CH3:3])[CH3:1])[CH:5]=1)[C:1]#[N:8]

Participants

5

Reactant 2

HCID 7505BenzonitrileHCID 2723923Ammonium formate

Product 1

HCID 210972973-Amino-5-(tert-butyl)-2-methoxybenzonitrileYield 153.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

The above benzonitrile (100 mg, 0.427 mmol) was dissolved in 1:1 ethyl acetate/methanol (10 mL) in a nitrogen-flushed flask. Ammonium formate (270 mg, 4.27 mmol) and palladium on carbon (30 mg, 10% wet) were added and the mixture was heated to reflux for 30 min. The reaction was cooled to room temperature and filtered through a pad of diatomaceous earth, eluting with ethyl acetate. The ethyl acetate was evaporated under vacuum. The resulting residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes) to afford the title compound, (67 mg, 77%) as a colorless oil.

Workup

  1. customflushed flask
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 30 min
  4. filtrationfiltered through a pad of diatomaceous earth
  5. washeluting with ethyl acetate
  6. customThe ethyl acetate was evaporated under vacuum
  7. customThe resulting residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-962024312a2046778fa9897dfb10f51b
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

Loading…