Hydrochloric Acid → N-tert-butyl-3-nitropyridin-2-amine
Reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].Cl>CN1C(=O)CCC1>[C:11]([NH:15][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:14])([CH3:13])[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2-chloro-3-nitropyridine (5.0 g, 31.53 mmol) in anhydrous NMP (100 mL) was added tert-butylamine (10 mL, 94.52 mmol). The solution was heated at 60° C. for 14 hours and cooled. The mixture was poured into 1N HCl solution (400 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were washed with saturated NaHCO3 solution and dried over MgSO4. After filtration, the solvent was evaporated under vacuum to afford N-tert-butyl-3-nitropyridin-2-amine as dark brown syrup.
Workup
- temperaturecooled
- extractionextracted with EtOAc (3×150 mL)
- washThe combined organic layers were washed with saturated NaHCO3 solution
- dry with materialdried over MgSO4
- filtrationAfter filtration
- customthe solvent was evaporated under vacuum
Sources & evidence
- ORD record
- ord-2f8ab8c9909c46a689fae6ee8ebde42e
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232406B2
Reaction notes
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