Potassium Carbonate → {4-[2-Methoxy-4-(methylamino)-5-nitrophenoxy] (2-pyridyl)}-n-methylcarboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH:9][CH3:10])[C:6]([N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[OH:14].CC(C)([O-])C.[K+].Cl[C:22]1C=[C:24]([C:28]([NH:30][CH3:31])=[O:29])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C[N:39](C)C(=O)C>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH:9][CH3:10])[C:6]([N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][C:26]1[CH:27]=[CH:22][N:39]=[C:24]([C:28]([NH:30][CH3:31])=[O:29])[CH:25]=1Participants
Procedure
To a stirred solution of 2-methoxy-4-(methylamino)-5-nitrophenol(1 eq) in N,N-dimethylacetamide was added potassium-t-butoxide (1.2 eq) and continued stirring at ambient temperature until it solidified. To it was then added (3-chlorophenyl)-N-methylcarboxamide (1 eq) and anhydrous potassium carbonate (1 eq) and the resulting mixture was heated to 50° C. whereby the solid liquified. It was then heated to 110° C. for 12 h. After cooling to ambient temperature the solvent was distilled off and the resulting solid was extracted using ethyl acetate in a soxhlet apparatus for 48 h. the organic layer was cooled to 0° C., when the product crystallized from the ethyl acetate to give {4-[2-methoxy-4-(methylamino)-5-nitrophenoxy](2-pyridyl)}-N-methylcarboxamide. MS:MH+ 332
Workup
- temperatureIt was then heated to 110° C. for 12 h
- temperatureAfter cooling to ambient temperature the solvent
- distillationwas distilled off
- extractionthe resulting solid was extracted
- customfor 48 h.
- temperaturewas cooled to 0° C.
- customwhen the product crystallized from the ethyl acetate
Sources & evidence
- ORD record
- ord-7dedb8c1722640c2ab736f437c5820fd
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071216B2
Reaction notes
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