N-(6-chloro-3-iodopyridin-2-yl)pivalamide → 2-Amino-6-chloro-3-iodopyridine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C(C)(C)C)[C:5]([I:15])=[CH:4][CH:3]=1>Cl.CO>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([I:15])=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
N-(6-Chloro-3-iodopyridin-2-yl)-2,2-dimethylpropionamide (33 g, 97 mmol) is dissolved in 1N HCl (300 mL) in the presence of catalytic amount of methanol (0.5 mL) at 0° C. The reaction mixture is heated at 110° C. for 5 h. After cooling, the reaction mixture is extracted with ethyl acetate (2×250 mL). The organic layers are separated and the solvent is evaporated to afford the title compound as a viscous liquid (24 g, 97%) which is used in the next step without purification.
Workup
- temperatureAfter cooling
- extractionthe reaction mixture is extracted with ethyl acetate (2×250 mL)
- customThe organic layers are separated
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-ee166f5672cf4e5a98f138071f19ef8b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073926B2
Reaction notes
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