Triethylamine → 2,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamide
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 2,6-dichloronicotinic acid (1.92 g), N,O-dimethylhydroxylamine hydrochloride (1.46 g) and triethylamine (2.1 mL) in N,N-dimethylformamide (30 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g), and then the reaction mixture was stirred at room temperature for 4 days. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous solution of potassium hydrogen sulfate and a saturated aqueous solution of sodium hydrogen carbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.61 g) as a white solid.
Workup
- washwashed with 5% aqueous solution of potassium hydrogen sulfate
- dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-3b121e9ed3dd41989ab6aea15ce1edc3
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987473B2
Reaction notes
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