2-acetyl-3,4-dihydro-2H-naphthalen-1-one

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetyl-1-tetralone (5.0 g) was added into a mixture of potassium carbonate (3.8 g) and acetonitrile (60 ml). The mixture was stirred at 60° C. for 30 minutes and benzyl chloride was added and the stirring was continued at 60° C. for 5 hours. The mixture was filtered and evaporated. The yield was 7.2 g and was used for further reactions without purification. the stirring was continued at 60° C. for 5 hours The mixture was filtered evaporated The yield was 7.2 g and was used for further reactions without purification

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetyl-1-tetralone (5.0 g) was added into a mixture of potassium carbonate (3.8 g) and acetonitrile (60 ml). The mixture was stirred at 60° C. for 30 minutes and benzyl chloride was added and the stirring was continued at 60° C. for 5 hours. The mixture was filtered and evaporated. The yield was 7.2 g and was used for further reactions without purification. the stirring was continued at 60° C. for 5 hours The mixture was filtered evaporated The yield was 7.2 g and was used for further reactions without purification

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-acetyl-1-tetralone (329 mg, 1.75 mmol) in ethanol (12 mL) was added 4-methoxyphenyl hydrazine hydrochloride. The stirred suspension was heated to 80° C. overnight. The reaction was cooled to room temperature and diluted with water (100 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg). LC-MS (C19H18N2O calculated 290) m/z 291 (M+H). The reaction was cooled to room temperature extracted with EtOAc (2×50 mL) The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine dried over Na2SO4 The solvent was removed under reduced pressure the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-acetyl-1-tetralone (329 mg, 1.75 mmol) in ethanol (12 mL) was added 4-methoxyphenyl hydrazine hydrochloride. The stirred suspension was heated to 80° C. overnight. The reaction was cooled to room temperature and diluted with water (100 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg). LC-MS (C19H18N2O calculated 290) m/z 291 (M+H). The reaction was cooled to room temperature extracted with EtOAc (2×50 mL) The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine dried over Na2SO4 The solvent was removed under reduced pressure the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetyl-1-tetralone (5.0 g) was added into a mixture of potassium carbonate (3.8 g) and acetonitrile (60 ml). The mixture was stirred at 60° C. for 30 minutes and benzyl chloride was added and the stirring was continued at 60° C. for 5 hours. The mixture was filtered and evaporated. The yield was 7.2 g and was used for further reactions without purification. the stirring was continued at 60° C. for 5 hours The mixture was filtered evaporated The yield was 7.2 g and was used for further reactions without purification

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-acetyl-1-tetralone (329 mg, 1.75 mmol) in ethanol (12 mL) was added 4-methoxyphenyl hydrazine hydrochloride. The stirred suspension was heated to 80° C. overnight. The reaction was cooled to room temperature and diluted with water (100 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg). LC-MS (C19H18N2O calculated 290) m/z 291 (M+H). The reaction was cooled to room temperature extracted with EtOAc (2×50 mL) The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine dried over Na2SO4 The solvent was removed under reduced pressure the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-acetyl-1-tetralone (329 mg, 1.75 mmol) in ethanol (12 mL) was added 4-methoxyphenyl hydrazine hydrochloride. The stirred suspension was heated to 80° C. overnight. The reaction was cooled to room temperature and diluted with water (100 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg). LC-MS (C19H18N2O calculated 290) m/z 291 (M+H). The reaction was cooled to room temperature extracted with EtOAc (2×50 mL) The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine dried over Na2SO4 The solvent was removed under reduced pressure the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetyl-1-tetralone (5.0 g) was added into a mixture of potassium carbonate (3.8 g) and acetonitrile (60 ml). The mixture was stirred at 60° C. for 30 minutes and benzyl chloride was added and the stirring was continued at 60° C. for 5 hours. The mixture was filtered and evaporated. The yield was 7.2 g and was used for further reactions without purification. the stirring was continued at 60° C. for 5 hours The mixture was filtered evaporated The yield was 7.2 g and was used for further reactions without purification