N-(3-chlorophenyl)-2-cyanoacetamide

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

Procedure: The reaction of 4, 5-dihydroxy-2-nitrobenzaldehyde (185 mg, 1.01 mmol) and N-(3-chlorophenyl) cyanoacetamide (197 mg, 1.01 mmol) was effected in the same manner as in Example 1 to give the objective N-(3-chlorophenyl)-2-cyano-3-(4, 5-dihydroxy-2-nitrophenyl)propenamide (100 mg, 28% in yield) as brown powdery crystals.

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

Procedure: The reaction was effected in the same manner as in Example 1 with 5-fluorovanillin (410 mg, 2.41 mmol) and N-(3-chlorophenyl) cyanoacetamide (469 mg, 2.41 mmol) to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4-hydroxy-5-methoxyphenyl) propenamide (476 mg, 57% in yield) as yellow powders.

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

Procedure: The reaction was effected in the same manner as in Example 1 with 5-fluorovanillin (410 mg, 2.41 mmol) and N-(3-chlorophenyl) cyanoacetamide (469 mg, 2.41 mmol) to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4-hydroxy-5-methoxyphenyl) propenamide (476 mg, 57% in yield) as yellow powders.

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

Procedure: The reaction was performed in the same manner as in Example 1 with 5-bromovanillin (1.38 g, 5.97 mmol) and N-(3-chlorophenyl) cyanoacetamide (1.16 g, 5.97 mmol) to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4-hydroxy-5-methoxyphenyl) propenamide (1.58 g, 65% in yield).

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

Procedure: The reaction was performed in the same manner as in Example 1 with 5-bromovanillin (1.38 g, 5.97 mmol) and N-(3-chlorophenyl) cyanoacetamide (1.16 g, 5.97 mmol) to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4-hydroxy-5-methoxyphenyl) propenamide (1.58 g, 65% in yield).

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

Procedure: The reaction of 4, 5-dihydroxy-2-nitrobenzaldehyde (185 mg, 1.01 mmol) and N-(3-chlorophenyl) cyanoacetamide (197 mg, 1.01 mmol) was effected in the same manner as in Example 1 to give the objective N-(3-chlorophenyl)-2-cyano-3-(4, 5-dihydroxy-2-nitrophenyl)propenamide (100 mg, 28% in yield) as brown powdery crystals.

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

Procedure: The reaction was effected in the same manner as in Example 1 with 5-fluorovanillin (410 mg, 2.41 mmol) and N-(3-chlorophenyl) cyanoacetamide (469 mg, 2.41 mmol) to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4-hydroxy-5-methoxyphenyl) propenamide (476 mg, 57% in yield) as yellow powders.

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

Procedure: The reaction was performed in the same manner as in Example 1 with 5-bromovanillin (1.38 g, 5.97 mmol) and N-(3-chlorophenyl) cyanoacetamide (1.16 g, 5.97 mmol) to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4-hydroxy-5-methoxyphenyl) propenamide (1.58 g, 65% in yield).