2-Methoxyaniline → 4-Chloromethyl-N-(2-methoxyphenyl)benzamide
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[Cl:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[O:19])=[CH:16][CH:15]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
o-Anisidine (0.69 ml, 6.0 mmol) was dissolved in methylene chloride (10 ml) and, with cooling in an ice bath, mixed with 20% sodium hydroxide (5 ml) and 4-chloromethylbenzoyl chloride (1.17 g, 6.0 mmol). After 30 minutes of stirring at the same temperature, the reaction mixture was extracted with methylene chloride and then washed with 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting light beige solid was purified by recrystallization (ether-hexane) to obtain 1.56 g (94.2%) of the title compound in the form of colorless needle crystals.