Citric Acid → N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]-2-nitrobenzamide
Reaction equation
CC=CCO.[H-].[Na+].[CH:8]1([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:33])=[C:18]([NH:20][C:21](=[O:32])[C:22]3[CH:27]=[C:26](F)[CH:25]=[CH:24][C:23]=3[N+:29]([O-:31])=[O:30])[CH:19]=2)=[O:13])[CH2:10][CH2:9]1.C(O)(=O)[CH2:35][C:36]([CH2:41]C(O)=O)([C:38](O)=[O:39])O>CC(N(C)C)=O>[CH:8]1([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:33])=[C:18]([NH:20][C:21](=[O:32])[C:22]3[CH:27]=[C:26]([O:39][CH2:38][C:36]([CH3:41])=[CH2:35])[CH:25]=[CH:24][C:23]=3[N+:29]([O-:31])=[O:30])[CH:19]=2)=[O:13])[CH2:10][CH2:9]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methylallyl alcohol (3.6 ml) in anhydrous DMA (200 ml) was added sodium hydride (60% dispersion in oil, 6.7 g) and the solution stirred for 1 hour. N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-fluoro-2-nitrobenzamide (10 g) was added and the mixture stirred at room temperature for 18 hours. The mixture was poured into 1N citric acid (300 ml) and the precipitated solid filtered off under reduced pressure and dried in the vacuum oven to give N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]-2-nitrobenzamide as an orange solid (8.73 g); NMR Spectrum (DMSOd6) 0.6 (m, 2H), 0.7 (m, 2H), 1.9 (s, 3H), 2.3 (s, 1H), 2.9 (m, 1H), 4.7 (s, 2H), 5.1 (s, 1H), 5.2 (s, 1H), 7.2 (m, 3H), 7.6 (d, 1H), 7.9 (s, 1H), 8.2 (d, 1H), 8.4 (m, 1H), 10.1 (s, 1H); Mass Spectrum: M+H+ 408.
Workup
- stirringthe mixture stirred at room temperature for 18 hours
- filtrationthe precipitated solid filtered off under reduced pressure
- customdried in the vacuum oven
Sources & evidence
- ORD record
- ord-a40a0623aae64a0fa47804acfd5513be
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750154B2
Reaction notes
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