2-methoxybenzonitrile

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: Hydroxylamine (Fluka 55458; 50% in water; 11.28 mL; 187.76 mmol; 5 eq.) was added to a solution of 2-methoxybenzonitrile (Alrich 231231; 4.59 mL; 37.55 mmol; 1 eq.) in EtOH (50 mL) and the resulting mixture was stirred at room temperature for 16 hours then at 55° C. for 24 hours. The solvent was then evaporated and the resulting colourless oil was further dried under high vacuum to give a white solid. The latter was triturated in n-hexane, filtered and dried to afford the title compound (6.29 g, quantitative) as a white solid. at 55° C. for 24 hours The solvent was then evaporated the resulting colourless oil was further dried under high vacuum to give a white solid The latter was triturated in n-hexane filtered dried

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

Procedure: Add potassium hydroxide (30.3 g, 225 mmol) to a solution of 2-methoxybenzonitrile (25.0 g, 187 mmol) and hydroxylamine hydrochloride (15.77 g, 225 mmol) in ethanol (500 mL) at room temperature under nitrogen and heat the mixture at reflux for 12 hours. Remove the solvent under reduced pressure, triturate the residue with ethyl acetate/hexanes (1:9, 300 mL) and collect by vacuum filtration to provide N-hydroxy-2-methoxybenzamidine (24.0 g, 91%). heat the mixture at reflux for 12 hours Remove the solvent under reduced pressure triturate the residue with ethyl acetate/hexanes (1:9, 300 mL) collect by vacuum filtration

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

Procedure: Br2 (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71%). The mixture was refluxed for 29 h washed with saturated sodium bisulfite (50 mL), and brine (50 mL) The organic layer was dried over anhydrous sodium sulfate Evaporation of the solvent

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

Procedure: Br2 (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71%). The mixture was refluxed for 29 h washed with saturated sodium bisulfite (50 mL), and brine (50 mL) The organic layer was dried over anhydrous sodium sulfate Evaporation of the solvent

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

Procedure: Bromine (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71%). The mixture was refluxed for 29 h washed with saturated sodium bisulfite (50 mL), and brine (50 mL) The organic layer was dried over anhydrous sodium sulfate Evaporation of the solvent

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

Procedure: Bromine (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to the solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71%). The mixture was refluxed for 29 h washed with saturated sodium bisulfite (50 mL), and brine (50 mL) The organic layer was dried over anhydrous sodium sulfate Evaporation of the solvent

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

Procedure: Hydroxylamine (Fluka 55458; 50% in water; 11.28 mL; 187.76 mmol; 5 eq.) was added to a solution of 2-methoxybenzonitrile (Alrich 231231; 4.59 mL; 37.55 mmol; 1 eq.) in EtOH (50 mL) and the resulting mixture was stirred at room temperature for 16 hours then at 55° C. for 24 hours. The solvent was then evaporated and the resulting colourless oil was further dried under high vacuum to give a white solid. The latter was triturated in n-hexane, filtered and dried to afford the title compound (6.29 g, quantitative) as a white solid. at 55° C. for 24 hours The solvent was then evaporated the resulting colourless oil was further dried under high vacuum to give a white solid The latter was triturated in n-hexane filtered dried

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

Procedure: A mixture of 1-cyano-2-methoxybenzene (1.02 g, 7.7 mmol) and tributyltin azide (3.4 g, 10.0 mmol) in 3.0 mL of xylene was heated under reflux for 5 hours. The reaction mixture then was cooled and diluted with diethyl ether. Anhydrous hydrochloric acid was bubbled into the mixture and a white precipitate formed. The precipitate was collected by suction filtration and washed repeatedly with diethyl ether. Drying gave 5-(2-methoxyphenyl)-2H-tetrazole (1.33 g, 7.55 mmol). was heated under reflux for 5 hours The reaction mixture then was cooled Anhydrous hydrochloric acid was bubbled into the mixture a white precipitate formed The precipitate was collected by suction filtration washed repeatedly with diethyl ether Drying

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

Procedure: A mixture of 1-cyano-2-methoxybenzene (1.02 g, 7.7 mmol) and tributyltin azide (3.4 g, 10.0 mmol) in 3.0 mL of xylene was heated under reflux for hours. The reaction mixture then was cooled and diluted with diethyl ether. Anhydrous hydrochloric acid was bubbled into the mixture and a white precipitate formed. The precipitate was collected by suction filtration and washed repeatedly with diethyl ether. Drying gave 5-(2-methoxyphenyl)-2H-tetrazole (1.33 g, 7.55 mmol). was heated under reflux for hours The reaction mixture then was cooled Anhydrous hydrochloric acid was bubbled into the mixture a white precipitate formed The precipitate was collected by suction filtration washed repeatedly with diethyl ether Drying

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