Salicylic Acid → N-(4-Methoxyphenyl)-2-hydroxybenzamide
Reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(Cl)(=O)C(Cl)=O.C([N:19]([CH2:22][CH3:23])CC)C.C(Cl)(=O)C1C=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1>C(Cl)Cl.CN(C)C=O>[CH3:32][O:31][C:28]1[CH:29]=[CH:23][C:22]([NH:19][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[CH:26][CH:27]=1Participants
Procedure
To a solution of salicylic acid (1.38 g, 10.0 mmol) in methylene chloride (100 mL) cooled to 0° C. was added a few drops of dry N,N-dimethylformamide, followed by oxalyl chloride (1.41 mL). After 39 min, the ice bath was removed, and the reaction mixture allowed to warm to room temperature over 2 h. The solvent was removed in vacuo, and the residue dissolved in dry methylene chloride (125 mL). After cooling the solution to 0° C., triethylamine (2.81 mL, 20.0 mmol) was added, followed by the dropwise addition of a solution of p-anisoyl chloride (2.46 g, 20.0 mmol) in methylene chloride (25 mL). After 1 h, the reaction mixture was washed twice with 1 N aqueous hydrochloric acid and once with cold saturated aqueous sodium bicarbonate solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Trituration with hexane, produced 1.95 g (80%) of the title compound as a crystalline solid.
Workup
- customthe ice bath was removed
- customThe solvent was removed in vacuo
- dissolutionthe residue dissolved in dry methylene chloride (125 mL)
- temperatureAfter cooling the solution to 0° C.
- waitAfter 1 h
- washthe reaction mixture was washed twice with 1 N aqueous hydrochloric acid and once with cold saturated aqueous sodium bicarbonate solution
- dry with materialThe organic layer was dried (magnesium sulfate)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a158a20cb9ef4a178bc3bc046c3a1591
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313122B1
Reaction notes
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