2-(Phenylamino)phenol

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

Procedure: Hydrogen tetrafluoroborate (6.79 mL, 48% w/w) was added drop wise to a solution of 2-(phenylamino)phenol (9 g, 48.6 mmol) in 30 mL methanol. After 30 minutes of stirring, the solvent was removed under vacuum and (EtO)3CH (30 mL) was added. The resulting solution was stirred at room temperature under N2 overnight to give a white suspension. The solid was filtered and washed with diethyl ether to give 10 g of product (72%). the solvent was removed under vacuum and (EtO)3CH (30 mL) was added The resulting solution was stirred at room temperature under N2 overnight to give a white suspension The solid was filtered washed with diethyl ether

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 L three neck flask was charged with pyridinium chloride (52.2 g, 452 mmol) and 2-methoxy-N-phenylaniline (9 g, 45.2 mmol). The reaction mixture was heated to 200° C. for 4 hours. The reaction mixture was poured into 5% HCl (200 mL) and extracted with EtOAc (3×300 mL). The organic portion was combined and purified by column chromatography (100% DCM) to yield the desired product. (6.5 g, 77%) extracted with EtOAc (3×300 mL) purified by column chromatography (100% DCM)

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

Procedure: Hydrogen tetrafluoroborate (6.79 mL, 48% w/w) was added drop wise to a solution of 2-(phenylamino)phenol (9 g, 48.6 mmol) in 30 mL methanol. After 30 minutes of stirring, the solvent was removed under vacuum and (EtO)3CH (30 mL) was added. The resulting solution was stirred at room temperature under N2 overnight to give a white suspension. The solid was filtered and washed with diethyl ether to give 10 g of product (72%). the solvent was removed under vacuum and (EtO)3CH (30 mL) was added The resulting solution was stirred at room temperature under N2 overnight to give a white suspension The solid was filtered washed with diethyl ether

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 L three neck flask was charged with pyridinium chloride (52.2 g, 452 mmol) and 2-methoxy-N-phenylaniline (9 g, 45.2 mmol). The reaction mixture was heated to 200° C. for 4 hours. The reaction mixture was poured into 5% HCl (200 mL) and extracted with EtOAc (3×300 mL). The organic portion was combined and purified by column chromatography (100% DCM) to yield the desired product. (6.5 g, 77%) extracted with EtOAc (3×300 mL) purified by column chromatography (100% DCM)

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 L three neck flask was charged with pyridinium chloride (52.2 g, 452 mmol) and 2-methoxy-N-phenylaniline (9 g, 45.2 mmol). The reaction mixture was heated to 200° C. for 4 hours. The reaction mixture was poured into 5% HCl (200 mL) and extracted with EtOAc (3×300 mL). The organic portion was combined and purified by column chromatography (100% DCM) to yield the desired product. (6.5 g, 77%) extracted with EtOAc (3×300 mL) purified by column chromatography (100% DCM)

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

Procedure: Hydrogen tetrafluoroborate (6.79 mL, 48% w/w) was added drop wise to a solution of 2-(phenylamino)phenol (9 g, 48.6 mmol) in 30 mL methanol. After 30 minutes of stirring, the solvent was removed under vacuum and (EtO)3CH (30 mL) was added. The resulting solution was stirred at room temperature under N2 overnight to give a white suspension. The solid was filtered and washed with diethyl ether to give 10 g of product (72%). the solvent was removed under vacuum and (EtO)3CH (30 mL) was added The resulting solution was stirred at room temperature under N2 overnight to give a white suspension The solid was filtered washed with diethyl ether

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 L three neck flask was charged with pyridinium chloride (52.2 g, 452 mmol) and 2-methoxy-N-phenylaniline (9 g, 45.2 mmol). The reaction mixture was heated to 200° C. for 4 hours. The reaction mixture was poured into 5% HCl (200 mL) and extracted with EtOAc (3×300 mL). The organic portion was combined and purified by column chromatography (100% DCM) to yield the desired product. (6.5 g, 77%) extracted with EtOAc (3×300 mL) purified by column chromatography (100% DCM)