Pyridine → 5-Methoxybenzene-1,3-dicarbonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([NH2:14])=O)[CH:6]=[C:7]([CH:11]=1)[C:8]([NH2:10])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]#[N:14])[CH:6]=[C:7]([CH:11]=1)[C:8]#[N:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of the 5-methoxyisophthalamide (3.1 g, 16 mmol) in a dichloromethane (27 mL) at 0° C. was treated with pyridine (5.2 mL, 65 mol) and then trifluoroacetic anhydride drop-wise (5.4 mL, 39 mmol). The reaction was stirred at 0° C. for 20 minutes and then stirred overnight at ambient temperature. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Silica gel chromatography using hexanes:ethyl acetate:dichloromethane afforded 940 mg (46%) of the 5-methoxyisophthalonitrile as a white solid.
Workup
- stirringstirred overnight at ambient temperature
- washThe reaction mixture was washed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0d45eb141f164b05873630dcc9427728
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06660753B2
Reaction notes
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