Hydrochloric Acid → 5-Chloro-6-methylpyridine-2-carbonitrile
Reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8].[ClH:11]>CC#N.Cl[Cu]>[Cl:11][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A solution of 5-amino-6-methylpicolinonitrile (2) (260 mg, 1.95 mmol), CuCl (290 mg, 2.93 mmol) and t-BuONO (456 mg, 3.9 mmol) in CH3CN (10 mL) was stirred at room temperature under N2 for 2 h, and then warmed to 60° C. After 2 h, 10 mL 6N HCl was added and extracted with EA (3×10 mL). The organic phase was dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by Prep-TLC using PE/EtOAc=1/1 to give title compound as oil.
Workup
- extractionextracted with EA (3×10 mL)
- dry with materialThe organic phase was dried with anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by Prep-TLC
Sources & evidence
- ORD record
- ord-9f23e741220f48faaf969e926c077df4
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353104B2
Reaction notes
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