(2-methoxyphenyl)hydrazine

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

Procedure: In analogy to Example 187, step 1, 2-methoxyphenylhydrazine was reacted with 2,5-dibromobenzaldehyde to give the title compound as a brown oil. MS (m/e)=303.2 [M+H+].

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methoxyphenylhydrazine (14.07 g, 81 mmol) in EtOH (100 mL) was added dropwise to a refluxing solution of 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (10 g, 53.7 mmol) in toluene (100 mL), under an argon atmosphere. The reaction mixture was stirred for 18 h at 100° C., allowed to cool to rt, concentrated, diluted with a saturated aqueous solution of sodium bicarbonate (250 mL), and extracted with EtOAc. The organic extracts were washed with a saturated aqueous solution of sodium bicarbonate, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→7:3) to provide 10.1 g of the title compound. tR: 1.11 min (LC-MS 4); to cool to rt concentrated diluted with a saturated aqueous solution of sodium bicarbonate (250 mL) extracted with EtOAc The organic extracts were washed with a saturated aqueous solution of sodium bicarbonate dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→7:3)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methoxyphenylhydrazine (14.07 g, 81 mmol) in EtOH (100 mL) was added dropwise to a refluxing solution of 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (10 g, 53.7 mmol) in toluene (100 mL), under an argon atmosphere. The reaction mixture was stirred for 18 h at 100° C., allowed to cool to rt, concentrated, diluted with a saturated aqueous solution of sodium bicarbonate (250 mL), and extracted with EtOAc. The organic extracts were washed with a saturated aqueous solution of sodium bicarbonate, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→7:3) to provide 10.1 g of the title compound. tR: 1.11 min (LC-MS 4); to cool to rt concentrated diluted with a saturated aqueous solution of sodium bicarbonate (250 mL) extracted with EtOAc The organic extracts were washed with a saturated aqueous solution of sodium bicarbonate dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→7:3)

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

Procedure: The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-phenyl-1H-pyridazin-4-one (A-1) and 2-methoxy-phenylhydrazine×HCl according to the method described for Example 1 in 61% yield. MS: M=345.1 (M+H)+ The product was obtained

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

Procedure: In analogy to Example 187, step 1, 2-methoxyphenylhydrazine was reacted with 2,5-dibromobenzaldehyde to give the title compound as a brown oil. MS (m/e)=303.2 [M+H+].

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methoxyphenylhydrazine (14.07 g, 81 mmol) in EtOH (100 mL) was added dropwise to a refluxing solution of 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (10 g, 53.7 mmol) in toluene (100 mL), under an argon atmosphere. The reaction mixture was stirred for 18 h at 100° C., allowed to cool to rt, concentrated, diluted with a saturated aqueous solution of sodium bicarbonate (250 mL), and extracted with EtOAc. The organic extracts were washed with a saturated aqueous solution of sodium bicarbonate, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→7:3) to provide 10.1 g of the title compound. tR: 1.11 min (LC-MS 4); to cool to rt concentrated diluted with a saturated aqueous solution of sodium bicarbonate (250 mL) extracted with EtOAc The organic extracts were washed with a saturated aqueous solution of sodium bicarbonate dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→7:3)