Dimethylformamide → N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide
Reaction equation
FC1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH3:12][Si]([N-][Si](C)(C)C)(C)C.[K+].OC1C=[C:25]([C:29]([NH:31][CH3:32])=O)[CH:26]=[CH:27]C=1.[C:33](=[O:36])([O-])[O-].[K+].[K+].[CH3:39][N:40](C)[CH:41]=[O:42]>>[CH3:39][NH:40][C:41]([C:29]1[CH:25]=[C:26]([O:36][C:33]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:8][CH3:12])[CH:7]=2)[CH:27]=[CH:32][N:31]=1)=[O:42]Participants
Conditions
- Temperature
- 90 °C
Procedure
The mixture containing 5-fluro-2-nitrophenylamine (1 eq), Potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (3-hydroxyphenyl)-N-methylcarboxamide (1 eq) and Potassium carbonate (1.2 eq) and stirred at 90° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel gave N-methyl {4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide. It was taken in methanol and hydrogenated with catalytic amount of 10% Pd/C to give {4-[4-amino-3-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide. MS: MH+=272.
Workup
- concentrationThe reaction mixture was then concentrated
- custompartitioned between ethyl acetate and water
- customThe organic layer was separated
- washwashed with brine
- customdried
- filtrationfiltered
- concentrationconcentrated in vacuum
- customto give brown solid
- customPurification on silica gel
Sources & evidence
- ORD record
- ord-40acfaf085a14c889f79846a72fdd46b
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071216B2
Reaction notes
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