Sodium Bicarbonate → 6-Chloro-5-methylpyridin-2-amine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C(C)(C)C)[CH:5]=[CH:4][C:3]=1[CH3:15].C([O-])(O)=O.[Na+]>Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To N-(6-chloro-5-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide (4.00 g, 17.7 mmol) was added 6 N HCl (20 mL) at room temperature. The mixture was stirred at 80° C. for 12 hours. The reaction mixture was basified with drop-wise addition of sat. NaHCO3 to pH 8-9, and then the mixture was extracted with CH2Cl2 (3×). The organic phases were dried over Na2SO4 and evaporated under vacuum to obtain the 6-chloro-5-methyl-pyridin-2-ylamine (900 mg, 36%). 1H NMR (400 MHz, CDCl3) δ 7.28 (d, J=8.0 Hz, 1H), 6.35 (d, J=8.0 Hz, 1H), 4.39 (br s, 2H), 2.22 (s, 3H). MS (ESI) m/z: 143 (M+H+).
Workup
- extractionthe mixture was extracted with CH2Cl2 (3×)
- dry with materialThe organic phases were dried over Na2SO4
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-28fa88bfc1ad4a69b4f924a706c512ba
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318733B2
Reaction notes
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