Water → 6-Chloro-N-cyclopropyl-3-nitropyridin-2-amine
Reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Cl[C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[N:7]=1.O>C1(C)C=CC=CC=1>[Cl:15][C:8]1[N:7]=[C:6]([NH:4][CH:1]2[CH2:3][CH2:2]2)[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of cyclopropylamine (1.25 g, 22.0 mmol) in toluene (11 mL) was added over 10 min to an ice-cold solution of 2,6-dichloro-3-nitropyridine (2.00 g, 10.4 mmol) in toluene (10 mL). The mixture was stirred at 0° C. for 1 h and at room temperature for 2 h. Water (50 mL) was added to the mixture and the phases were separated. The organic layer was washed with brine (25 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 3:2) to give the title compound (1.97 g, 89% yield) as a yellow solid.
Workup
- customthe phases were separated
- washThe organic layer was washed with brine (25 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography (hexane:EtOAc, 3:2)
Sources & evidence
- ORD record
- ord-91fbc7135f24407aa85e1a68147d73df
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420359B1
Reaction notes
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