2,6-Dichloro-N-methoxy-N-methylisonicotinamide → 1-(2,6-Dichloropyridin-4-YL)ethanone
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:14])[N:13]=1)[C:5](N(OC)C)=[O:6].[CH3:15][Li]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH3:15])[CH:11]=[C:12]([Cl:14])[N:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
2,6-Dichloro-N-methoxy-N-methylisonicotinamide (Intermediate 47, 780 mg, 3.3 mmol) in anhydrous diethylether (13 ml) was cooled to −78° C. Methyllithium (1.6 M solution in diethyl ether (5.2 ml, 8.3 mmol) was added dropwise. The mixture was stirred at −78° C. for 1 h and quenched with ammonium chloride solution, followed by warming to room temperature. The reaction mixture was diluted with water (20 ml) and extracted with diethyl ether (2×30 ml), dried over sodium sulphate and concentrated in vacuo to give the title compound (575 mg).
Workup
- customquenched with ammonium chloride solution
- temperatureby warming to room temperature
- additionThe reaction mixture was diluted with water (20 ml)
- extractionextracted with diethyl ether (2×30 ml)
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6a4c20284b47467fb1d3ba448ad8f26e
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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