5-amino-2-methoxybenzonitrile

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

Procedure: A solution of sodium nitrite (4.0 g) in water (7 ml) was added to an ice cooled mixture of 3-cyano-4-methoxyaniline (7.7 g) and concentrated hydrochloric acid (21 ml). The mixture was stirred at 0° C. for 30 minutes. To the resultant mixture a solution of tin(II) chloride dihydrate (49 g) and concentrated hydrochloric acid (5 ml) was added at 0° C. and stirred for 1 hour. The precipitates were filtered and washed with ice cooled concentrated hydrochloric acid (10 ml) to give crude (3-cyano-4-methoxyphenyl)hydrazine hydrochloride (14.8 g). cooled stirred for 1 hour The precipitates were filtered washed with ice cooled concentrated hydrochloric acid (10 ml)

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

Procedure: A mixture of 2-methoxy-5-nitrobenzonitrile (14 g), ammonium chloride (5 g), the powder of reduced iron (9 g) in methanol was refluxed for 4 hours and cooled. The reaction mixture was filtered and the filtrate was poured into water. The resultant precipitates were filtered and washed with water to give 3-cyano-4-methoxyaniline (7.7 g). cooled The reaction mixture was filtered the filtrate was poured into water The resultant precipitates were filtered washed with water

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

Procedure: A mixture of 2-methoxy-5-nitrobenzonitrile (14 g), ammonium chloride (5 g), the powder of reduced iron (9 g) in methanol was refluxed for 4 hours and cooled. The reaction mixture was filtered and the filtrate was poured into water. The resultant precipitates were filtered and washed with water to give 3-cyano-4-methoxyaniline (7.7 g). cooled The reaction mixture was filtered the filtrate was poured into water The resultant precipitates were filtered washed with water

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

Procedure: A solution of sodium nitrite (4.0 g) in water (7 ml) was added to an ice cooled mixture of 3-cyano-4-methoxyaniline (7.7 g) and concentrated hydrochloric acid (21 ml). The mixture was stirred at 0° C. for 30 minutes. To the resultant mixture a solution of tin(II) chloride dihydrate (49 g) and concentrated hydrochloric acid (5 ml) was added at 0° C. and stirred for 1 hour. The precipitates were filtered and washed with ice cooled concentrated hydrochloric acid (10 ml) to give crude (3-cyano-4-methoxyphenyl)hydrazine hydrochloride (14.8 g). cooled stirred for 1 hour The precipitates were filtered washed with ice cooled concentrated hydrochloric acid (10 ml)

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

Procedure: A mixture of 2-methoxy-5-nitrobenzonitrile (14 g), ammonium chloride (5 g), the powder of reduced iron (9 g) in methanol was refluxed for 4 hours and cooled. The reaction mixture was filtered and the filtrate was poured into water. The resultant precipitates were filtered and washed with water to give 3-cyano-4-methoxyaniline (7.7 g). cooled The reaction mixture was filtered the filtrate was poured into water The resultant precipitates were filtered washed with water