Ammonia → 3-Aminopyridine-2-carbonitrile
Reaction equation
F[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH3:10]>CS(C)=O.C(Cl)(Cl)Cl>[NH2:10][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
A solution of 3-fluoro-2-cyanopyridine (Sakamoto et. al., Chem. Pharm. Bull. 1985, 33: 565-571) (10 g, 82 mmol) in DMSO (30 mL) was placed in a pressure vessel and saturated with ammonia gas. The reaction was capped and heated to 70 degrees C. overnight. The reaction was cooled, vented and re-saturated with ammonia, then sealed and re-heated for several hours. The reaction was cooled, vented, diluted with CHCl3 and the solids that had formed were filtered off. The solution was added to the top of a silica gel column (150 mm×7 inches) saturated with CHCl3 and the column was eluted with a gradient of 100% CHCl3 to 100% CHCl3 saturated with NH3. The fractions were collected and concentrated to give the product which contained some residual DMSO. This was used a in the next step.
Workup
- customThe reaction was capped
- customovernight
- temperatureThe reaction was cooled
- customsealed
- temperaturere-heated for several hours
- temperatureThe reaction was cooled
- customthe solids that had formed
- filtrationwere filtered off
- additionThe solution was added to the top of a silica gel column (150 mm×7 inches) saturated with CHCl3
- washthe column was eluted with a gradient of 100% CHCl3 to 100% CHCl3 saturated with NH3
- customThe fractions were collected
- concentrationconcentrated
- customto give the product which
Sources & evidence
- ORD record
- ord-b3856f4a76af42d7b21231d412ffcb7c
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279487B2
Reaction notes
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