Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.[OH-].[Na+].C[O:13][N:14]=O.S(=O)(=O)(O)O.N([O-])=O.[Na+]>CO.O>[N:14](=[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:8]#[N:9])[OH:13]Participants
8
Conditions
- Temperature
- 0 °C
Procedure
3-pyridylacetonitrile (47.2 g, 400 mmol) was dissolved in a solution of sodium hydroxide (16 g, 400 mmol) in methanol (100 ml). Methylnitrite, generated by dropping a solution of concentrated sulphuric acid (12.8 ml) and water (26 ml) to a solution of sodium nitrite (33.2 g, 480 mmol) in water (20 ml) and methanol (20 ml), was bobled through the 3-pyridylacetonitrile solution at 0° C. The reaction mixture was stirred at 0° C. for 1 h and the precipitate collected by filtration. The precipitate was washed with a little methanol to give the wanted product in 70% (41.1 g) yield. M+ : 147.
Workup
- filtrationthe precipitate collected by filtration
- washThe precipitate was washed with a little methanol
- customto give the wanted product in 70% (41.1 g)
- customyield
Sources & evidence
- ORD record
- ord-9293ee0603c248aebaa84c8d1a6140b2
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05260311
Linked notes
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