methyl 2-hydrazinylbenzoate

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

Procedure: A 150-mL round-bottom flask was placed a solution of methyl 2-hydrazinylbenzoate (7.81 g, 1.00 equiv, 1%) in AcOH (70 mL). To this solution was added cyclohexanone (4.5 g, 45.92 mmol, 1.00 equiv) dropwise with stirring at 80° C. The resulting solution was heated to reflux for 2 hr in an oil bath. Upon completion, the reaction was then quenched with water (50 mL). The solids were collected by filtration and washed with H2O (2×50 mL) affording methyl 6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate as white solid (6 g, 55.8%). A 150-mL round-bottom flask was placed The resulting solution was heated to reflux for 2 hr in an oil bath Upon completion, the reaction was then quenched with water (50 mL) The solids were collected by filtration washed with H2O (2×50 mL)

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

Procedure: A 150-mL round-bottom flask was placed a solution of methyl 2-hydrazinylbenzoate (7.81 g, 1.00 equiv, 1%) in AcOH (70 mL). To this solution was added cyclohexanone (4.5 g, 45.92 mmol, 1.00 equiv) dropwise with stirring at 80° C. The resulting solution was heated to reflux for 2 hr in an oil bath. Upon completion, the reaction was then quenched with water (50 mL). The solids were collected by filtration and washed with H2O (2×50 mL) affording methyl 6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate as white solid (6 g, 55.8%). A 150-mL round-bottom flask was placed The resulting solution was heated to reflux for 2 hr in an oil bath Upon completion, the reaction was then quenched with water (50 mL) The solids were collected by filtration washed with H2O (2×50 mL)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100-mL round-bottom flask was a solution of methyl 2-aminobenzoate (1 g, 6.62 mmol, 1.00 equiv) in HCl (30%, 10 mL). To this solution was added a solution of NaNO2 (500 mg, 7.25 mmol, 1.02 equiv) in H2O (10 mL) dropwise at 0° C. over 5 minutes. The resulting mixture was stirred at 0° C. for 30 minutes. Then, a solution of SnCl2.2H2O (2.75 g, 12.19 mmol, 2.00 equiv) in HCl (30%) (12 mL) was added dropwise at 0° C. The resulting solution was stirred for an additional 2 hours at room temperature. The solids were collected by filtration and washed with H2O (2×20 mL) affording methyl 2-hydrazinylbenzoate as white solid (0.6 g, 55%). A 100-mL round-bottom flask was The resulting solution was stirred for an additional 2 hours at room temperature The solids were collected by filtration washed with H2O (2×20 mL)

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

Procedure: A 150-mL round-bottom flask was placed a solution of methyl 2-hydrazinylbenzoate (7.81 g, 1.00 equiv, 1%) in AcOH (70 mL). To this solution was added cyclohexanone (4.5 g, 45.92 mmol, 1.00 equiv) dropwise with stirring at 80° C. The resulting solution was heated to reflux for 2 hr in an oil bath. Upon completion, the reaction was then quenched with water (50 mL). The solids were collected by filtration and washed with H2O (2×50 mL) affording methyl 6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate as white solid (6 g, 55.8%). A 150-mL round-bottom flask was placed The resulting solution was heated to reflux for 2 hr in an oil bath Upon completion, the reaction was then quenched with water (50 mL) The solids were collected by filtration washed with H2O (2×50 mL)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100-mL round-bottom flask was a solution of methyl 2-aminobenzoate (1 g, 6.62 mmol, 1.00 equiv) in HCl (30%, 10 mL). To this solution was added a solution of NaNO2 (500 mg, 7.25 mmol, 1.02 equiv) in H2O (10 mL) dropwise at 0° C. over 5 minutes. The resulting mixture was stirred at 0° C. for 30 minutes. Then, a solution of SnCl2.2H2O (2.75 g, 12.19 mmol, 2.00 equiv) in HCl (30%) (12 mL) was added dropwise at 0° C. The resulting solution was stirred for an additional 2 hours at room temperature. The solids were collected by filtration and washed with H2O (2×20 mL) affording methyl 2-hydrazinylbenzoate as white solid (0.6 g, 55%). A 100-mL round-bottom flask was The resulting solution was stirred for an additional 2 hours at room temperature The solids were collected by filtration washed with H2O (2×20 mL)