3-(dimethoxymethyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 1.06 g of 3-aminobenzaldehyde dimethyl acetal was dissolved in a mixture of 5 ml of toluene and 10 ml of water containing 0.8 g of sodium hydroxide, and 5 ml of a toluene solution of 1.3 g of benzoyl chloride was added. The mixture was stirred at room temperature for 2 hours. The organic layer was separated, and evaporated under reduced pressure. The residue was dissolved in a mixture of 10 ml of methanol and 10 ml of 10% hydrochloric acid, and heated at 90° C. for 30 minutes. Water (20 ml) was added to the reaction mixture to allow it to cool. There was obtained 1.16 g (yield 87.3%) of 3-benzoylaminobenzaldehyde as colorless needles having a melting point of 122° to 123° C. was added The organic layer was separated evaporated under reduced pressure The residue was dissolved in a mixture of 10 ml of methanol and 10 ml of 10% hydrochloric acid heated at 90° C. for 30 minutes Water (20 ml) was added to the reaction mixture to cool

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

Procedure: 1.06 g of 3-aminobenzaldehyde dimethyl acetal was dissolved in a mixture of 5 ml of toluene and 10 ml of water containing 0.8 g of sodium hydroxide, and 5 ml of a toluene solution of 1.3 g of benzoyl chloride was added. The mixture was stirred at room temperature for 2 hours. The organic layer was separated, and evaporated under reduced pressure. The residue was dissolved in a mixture of 10 ml of methanol and 10 ml of 10% hydrochloric acid, and heated at 90° C. for 30 minutes. Water (20 ml) was added to the reaction mixture to allow it to cool. There was obtained 1.16 g (yield 87.3%) of 3-benzoylaminobenzaldehyde as colorless needles having a melting point of 122° to 123° C. was added The organic layer was separated evaporated under reduced pressure The residue was dissolved in a mixture of 10 ml of methanol and 10 ml of 10% hydrochloric acid heated at 90° C. for 30 minutes Water (20 ml) was added to the reaction mixture to cool

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

Procedure: 334 mg of 3-aminobenzaldehyde dimethyl acetal was dissolved in 10 ml of anhydrous benzene, and 212 mg of benzaldehyde and 2 g of molecular sieve 4A (a product of Nippon Chromato Kogyo Co., Ltd.) were added. The mixture was stirred at room temperature for 4 hours. The molecular sieve was removed by filtration, and the filtrate was evaporated under reduced pressure. The residue was dissolved in 20 ml of methanol, and 100 mg of sodium borohydride was added. The mixture was stirred for 2 hours. The reaction mixture was diluted with water, and extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was recrystallized from hexane to give 451 mg (yield 87.7%) of 3-benzylaminobenzaldehyde dimethyl acetal having a melting point of 55° to 56° C. ) were added The molecular sieve was removed by filtration the filtrate was evaporated under reduced pressure The residue was dissolved in 20 ml of methanol 100 mg of sodium borohydride was added The mixture was stirred for 2 hours The reaction mixture was diluted with water extracted with ethyl ether The extract was dried over anhydrous sodium sulfate the solvent was evaporated The residue was recrystallized from hexane

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

Procedure: 334 mg of 3-aminobenzaldehyde dimethyl acetal was dissolved in 10 ml of anhydrous benzene, and 212 mg of benzaldehyde and 2 g of molecular sieve 4A (a product of Nippon Chromato Kogyo Co., Ltd.) were added. The mixture was stirred at room temperature for 4 hours. The molecular sieve was removed by filtration, and the filtrate was evaporated under reduced pressure. The residue was dissolved in 20 ml of methanol, and 100 mg of sodium borohydride was added. The mixture was stirred for 2 hours. The reaction mixture was diluted with water, and extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was recrystallized from hexane to give 451 mg (yield 87.7%) of 3-benzylaminobenzaldehyde dimethyl acetal having a melting point of 55° to 56° C. ) were added The molecular sieve was removed by filtration the filtrate was evaporated under reduced pressure The residue was dissolved in 20 ml of methanol 100 mg of sodium borohydride was added The mixture was stirred for 2 hours The reaction mixture was diluted with water extracted with ethyl ether The extract was dried over anhydrous sodium sulfate the solvent was evaporated The residue was recrystallized from hexane

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

Procedure: 334 mg of 3-aminobenzaldehyde dimethyl acetal was dissolved in 10 ml of anhydrous benzene, and 212 mg of benzaldehyde and 2 g of molecular sieve 4A (a product of Nippon Chromato Kogyo Co., Ltd.) were added. The mixture was stirred at room temperature for 4 hours. The molecular sieve was removed by filtration, and the filtrate was evaporated under reduced pressure. The residue was dissolved in 20 ml of methanol, and 100 mg of sodium borohydride was added. The mixture was stirred for 2 hours. The reaction mixture was diluted with water, and extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was recrystallized from hexane to give 451 mg (yield 87.7%) of 3-benzylaminobenzaldehyde dimethyl acetal having a melting point of 55° to 56° C. ) were added The molecular sieve was removed by filtration the filtrate was evaporated under reduced pressure The residue was dissolved in 20 ml of methanol 100 mg of sodium borohydride was added The mixture was stirred for 2 hours The reaction mixture was diluted with water extracted with ethyl ether The extract was dried over anhydrous sodium sulfate the solvent was evaporated The residue was recrystallized from hexane

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

Procedure: Using an analogous procedure to that described in Example 1, 2-(4-benzyloxy-2-methoxyphenyl)acetic acid was reacted with 3-(1,1-dimethoxymethyl)aniline to give N-[3-(1,1-dimethoxymethyl)phenyl]-2-(4-benzyloxy-2-methoxyphenyl)acetamide in 51% yield. The compound was obtained as a mixture of the dimethoxyacetal and the corresponding aldehyde.