Methanol → N-(2-Bromo-4-hydroxy-6-methylphenyl)-3-nitrobenzamide
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8]C(=O)C(C)(C)C)[CH:5]=[C:4]([CH3:15])[C:3]=1[NH:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1.[OH-].[Na+].CO>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:15])[C:3]=1[NH:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
N-(2-bromo-6-methyl-4-pivaloyloxyphenyl) 3-nitrobenzamide and an aqueous solution of sodium hydroxide were added to methanol, and the resulting mixture was stirred at 70° C. for 3 hours. The solvent was removed under a reduced pressure to obtain a residue. The resulting residue was dissolved in ethyl acetate, washed with aqueous 2N hydrochloric acid solution, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1) to obtain N-(2-bromo-6-methyl-4-hydroxyphenyl) 3-nitrobenzamide. Then, the desired title product was prepared according to the conditions as described in Example 1-3 (Yield: 97%).
Workup
- customThe solvent was removed under a reduced pressure
- customto obtain a residue
- washwashed with aqueous 2N hydrochloric acid solution
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under a reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1)
Sources & evidence
- ORD record
- ord-2057dda266644fa591e9a67f254dd933
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067638B2
Reaction notes
Loading…