Acetic Anhydride → Methyl 6-(acetylamino)nicotinate
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>CCOC(C)=O>[C:12]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:7]=1)(=[O:14])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a mixture of methyl 6-aminopyridine-3-carboxylate (3 g, 19.72 mmol, Aldrich) in 1,4-ioxane (50 mL) was added acetic anhydride (3.72 mL, 39.4 mmol, Aldrich). The resulting mixture was then heated at 85° C. for 3 h and at 100° C. for an additional 3 h. The mixture was then cooled to rt and diluted with EtOAc (400 mL). The mixture was then washed with saturated NaHCO3 solution (2×200 mL), brine (150 mL), dried over MgSO4, and concentrated in vacuo to afford the title compound as a white solid, which was used in the next step without purification. MS (ESI, positive ion) m/z: 195 (M+H).
Workup
- temperatureThe mixture was then cooled to rt
- washThe mixture was then washed with saturated NaHCO3 solution (2×200 mL), brine (150 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8f662cd2d77c43118c3c95a97eccb7f3
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096527B2
Reaction notes
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