Thionyl Chloride → 2,4-Dimethylpyridin-3-amine
Reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1C(O)=O.S(Cl)(Cl)=O.[N-:16]=[N+]=[N-].[Na+]>O>[CH3:1][C:2]1[C:3]([NH2:16])=[C:7]([CH3:11])[CH:8]=[CH:9][N:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 1a (0.98 g, 6.5 mmol) and thionyl chloride (5 ml) was heated to 60° C. for 1 hour. The mixture was concentrated to dryness. The mixture was then dissolved in acetone (10 ml) prior to the addition of NaN3 (0.65 g, 10 mmol) and water (5 ml). The solution was heated to 70° C. for 1 hour. Acetone was evaporated from the reaction mixture which was washed with brine and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated and chromatographed to yield 1b (0.585 g, 4.79 mmol, 74%).
Workup
- concentrationThe mixture was concentrated to dryness
- dissolutionThe mixture was then dissolved in acetone (10 ml)
- temperatureThe solution was heated to 70° C. for 1 hour
- customAcetone was evaporated from the reaction mixture which
- washwas washed with brine
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
- customchromatographed
Sources & evidence
- ORD record
- ord-161e9a64b288476da7e8ad850f7924be
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367684B2
Reaction notes
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