Acetic Anhydride → N-(3-cyanophenyl)acetamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10](OC(=O)C)(=[O:12])[CH3:11]>N1C=CC=CC=1>[C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:10](=[O:12])[CH3:11])[CH:9]=[CH:8][CH:7]=1)#[N:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
3-Aminobenzonitrile (5.70 g) and N,N-dimethylaminopyridine (20 mg) were dissolved in pyridine (40 ml) and the mixture was cooled to 5° C. Acetic anhydride (5.8 ml) was added and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure. Ethyl acetate and 1N hydrochloric acid were added to the residue, and the organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and saturated brine. The organic layer was dried, concentrated and recrystallized from hexane-ethyl acetate to give the title compound (5.78 g) as pale-brown powder crystals.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionEthyl acetate and 1N hydrochloric acid were added to the residue
- washthe organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and saturated brine
- customThe organic layer was dried
- concentrationconcentrated
- customrecrystallized from hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-e9549ad4074b4519ab995364bc8fef1f
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067537B2
Reaction notes
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