Dimethylformamide → 2-Amino-6-(2-furyl)nicotinonitrile
Reaction equation
[C:1]([C:3]1[C:4](OCC(N)=O)=[N:5][C:6]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].C[N:26](C)C=O>O.C(OCC)(=O)C>[NH2:26][C:4]1[N:5]=[C:6]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A suspension of 2-[[3-cyano-6-(2-furyl)-2-pyridyl]oxy]acetamide (8.0 g, 32.9 mmol) and potassium carbonate (9.1 g, 65.9 mmol) in N,N-dimethylformamide (80 ml) was stirred at 120° C. for 1.5 hours. After cooling as it was, the reaction solution was diluted with water and ethyl acetate, and the insoluble matters were filtered off. The aqueous layer in the filtrate was extracted with ethyl acetate. The combined organic layer was washed with an aqueous saturated solution of ammonium chloride (×2), dried over anhydrous sodium sulfate, and concentrated. The residue was suspended in methanol, and the resulting solid was collected by filtration and washed with methanol, to give the title compound (3.81 g, 63%) as a brown solid.
Workup
- temperatureAfter cooling as it
- filtrationthe insoluble matters were filtered off
- extractionThe aqueous layer in the filtrate was extracted with ethyl acetate
- washThe combined organic layer was washed with an aqueous saturated solution of ammonium chloride (×2)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- filtrationthe resulting solid was collected by filtration
- washwashed with methanol
Sources & evidence
- ORD record
- ord-5ebf9af27a2e463c8af4b8c63b4cc4a7
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06750232B2
Reaction notes
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