Sodium Hydroxide → 6-Methoxy-5-methylpyridin-2-amine
Reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH:11]C(=O)C)[CH:8]=[CH:7][C:6]=1[CH3:15]>CO.O>[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[CH3:15]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A 10% solution of aqueous NaOH (40 mL) was added to a solution of N-(6-methoxy-5-methylpyridin-2-yl)acetamide (2.21 g, 12.3 mmol) in MeOH (160 mL) and the reaction mixture was heated at 90° C. for 3 d. After cooling to rt and concentration in vacuo to remove the MeOH the aqueous residue was combined with that from a previous batch derived from N-(6-methoxy-5-methylpyridin-2-yl)acetamide (2.21 g, 12.3 mmol). The aqueous phase was diluted with H2O (40 mL) and extracted with DCM (3×150 mL). The combined organic phases were washed with brine, dried (Na2SO4) and combined with a previous batch of crude 6-methoxy-5-methylpyridin-2-amine (266 mg). Concentration in vacuo yielded the title compound (3.30 g, 23.9 mmol).
Workup
- temperatureAfter cooling to rt
- concentrationconcentration in vacuo
- customto remove the MeOH the aqueous residue
- extractionextracted with DCM (3×150 mL)
- washThe combined organic phases were washed with brine
- dry with materialdried (Na2SO4)
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-4a2b32b1f6ce4e7ca2ec7bd9a4bff329
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249160B2
Reaction notes
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