N-methylbenzanilide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Several model compounds were prepared for carbon-13 NMR studies for comparison with Polymer 5 in Example V. Phenyl benzoate, benzanilide, N-methylbenzanilide, and thiophenyl benzoate were prepared from benzoyl chloride and phenol, aniline, N-methylaniline, and thiophenol, respectively.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Several model compounds were prepared for carbon-13 NMR studies for comparison with Polymer 5 in Example V. Phenyl benzoate, benzanilide, N-methylbenzanilide, and thiophenyl benzoate were prepared from benzoyl chloride and phenol, aniline, N-methylaniline, and thiophenol, respectively.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.01 mmol of the complex 1 produced in Example 1 and 5 mmol of N-methyl-N-phenylbenzamide were placed in a 50 mL-autoclave equipped with a stirrer, and the autoclave was purged with nitrogen. 1.5 mL of Methanol and 2.5 mL of methanol solution of 2.0 M sodium methoxide were added to the autoclave, and the autoclave was purged with hydrogen. The resulting mixture was stirred under hydrogen atmosphere (5 MPa) and 100 degrees C. for 16 hours to obtain a reaction solution. After the completion of reaction, the reaction solution was cooled, diluted with 40 mL of dichloromethane, and subjected to silica gel filtration (eluting solvent: dichloromethane/methanol=10/1). The thus obtained solution was concentrated, and then the resulting residue was purified by silica gel column chromatography (silica gel: 40 g, hexane/ethyl acetate=8/1 to 4/1). As a result, benzyl alcohol (425 mg, 90%) and N-methyl-N-phenylamine (440 mg, 82%) were obtained. equipped with a stirrer the autoclave was purged with nitrogen 1.5 mL of Methanol and 2.5 mL of methanol solution of 2.0 M sodium methoxide were added to the autoclave the autoclave was purged with hydrogen for 16 hours to obtain a reaction solution After the completion of reaction the reaction solution was cooled subjected to silica gel filtration (eluting solvent: dichloromethane/methanol=10/1) The thus obtained solution was concentrated the resulting residue was purified by silica gel column chromatography (silica gel: 40 g, hexane/ethyl acetate=8/1 to 4/1)