4-chloro-2-methoxyaniline

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

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

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

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

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: 4-Chloro-2-methoxynitrobenzene (2.8 g, 14.9 mmol) was dissolved in MeOH (110 mL), then 5% platinum on carbon (0.61 g) was added and the reaction stirred under a H2 balloon for 4 hours. The reaction was then filtered through diatomaceous earth (Celite®) and concentrated under vacuum, giving the product (2.3 g, 100%) as syrup that slowly solidified. MS (DCI) m/e 158 & 160 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.83 (d, J=2.4 Hz, 1H), 6.71 (dd, J=8.5, 2.4 Hz, 1H), 6.63 (d, J=8.5 Hz, 1H), 5.27 (v br s, 2H), 3.77 (s, 3H). The reaction was then filtered through diatomaceous earth (Celite®) concentrated under vacuum

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

Procedure: 4-Chloro-2-methoxynitrobenzene (2.8 g, 14.9 mmol) was dissolved in MeOH (110 mL), then 5% platinum on carbon (0.61 g) was added and the reaction stirred under a H2 balloon for 4 hours. The reaction was then filtered through diatomaceous earth (Celite®) and concentrated under vacuum, giving the product (2.3 g, 100%) as syrup that slowly solidified. MS (DCI) m/e 158 & 160 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.83 (d, J=2.4 Hz, 1H), 6.71 (dd, J=8.5, 2.4 Hz, 1H), 6.63 (d, J=8.5 Hz, 1H), 5.27 (v br s, 2H), 3.77 (s, 3H). The reaction was then filtered through diatomaceous earth (Celite®) concentrated under vacuum

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

Procedure: The title compound was prepared by substituting bromobenzene and 2-amino-5-chloroanisole for Example 189A and 4-aminopyridine, respectively, in Example 191. MS (ESI) m/e 234 (M+H)+.

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

Procedure: The title compound was prepared by substituting bromobenzene and 2-amino-5-chloroanisole for Example 189A and 4-aminopyridine, respectively, in Example 191. MS (ESI) m/e 234 (M+H)+.

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

Procedure: The title compound was prepared by substituting 4-bromopyridine and 2-amino-5-chloroanisole for Example 189A and 4-aminopyridine, respectively, in Example 191. MS (ESI) m/e 235 (M+H)+.

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

Procedure: The title compound was prepared by substituting 4-bromopyridine and 2-amino-5-chloroanisole for Example 189A and 4-aminopyridine, respectively, in Example 191. MS (ESI) m/e 235 (M+H)+.