2-Amino-6-methylpyridine → 2-Amino-5-chloro-6-methylpyridine
Reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Cl:16])C(=O)C1>CN(C=O)C>[Cl:16][C:3]1[CH:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 6-methylpyridin-2-amine (10.80 g, 100 mmol) in 50 mL of dry DMF was added a solution of NCS (13.4 g, 100 mmol) in 60 mL of dry DMF dropwise at 0° C. over 20 min. The resulting brown yellow solution was stirred at 0° C. for 1 hour, and at room temperature for 3 hours, then poured to 300 mL of ice-water. The resulting mixture was extracted with EtOAc, washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified via column chromatograph to afford 5-chloro-6-methylpyridin-2-amine.
Workup
- waitat room temperature for 3 hours
- extractionThe resulting mixture was extracted with EtOAc
- washwashed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was purified via column chromatograph
Sources & evidence
- ORD record
- ord-5ef099450cde4aa19e5ad1dfcc57f0c6
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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