2-(4-chlorophenyl)propanedial

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

Procedure: Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malondialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 ml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%). heated to reflux under nitrogen, for 18 h The resultant dark solution was cooled poured onto ice-water (150 ml) the mixture extracted with ethyl acetate (150 ml The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml) dried (Na2SO4) evaporated to dryness under reduced pressure the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent

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

Procedure: Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malon-dialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 nml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%). heated to reflux under nitrogen, for 18 h The resultant dark solution was cooled poured onto ice-water (150 ml) the mixture extracted with ethyl acetate (150 ml The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml) dried (Na2SO4) evaporated to dryness under reduced pressure the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent

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

Procedure: Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malon-dialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 nml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%). heated to reflux under nitrogen, for 18 h The resultant dark solution was cooled poured onto ice-water (150 ml) the mixture extracted with ethyl acetate (150 ml The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml) dried (Na2SO4) evaporated to dryness under reduced pressure the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent

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

Procedure: Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malondialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 ml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%). heated to reflux under nitrogen, for 18 h The resultant dark solution was cooled poured onto ice-water (150 ml) the mixture extracted with ethyl acetate (150 ml The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml) dried (Na2SO4) evaporated to dryness under reduced pressure the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent

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

Procedure: Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malondialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 ml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%). heated to reflux under nitrogen, for 18 h The resultant dark solution was cooled poured onto ice-water (150 ml) the mixture extracted with ethyl acetate (150 ml The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml) dried (Na2SO4) evaporated to dryness under reduced pressure the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent

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

Procedure: Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malon-dialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 nml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%). heated to reflux under nitrogen, for 18 h The resultant dark solution was cooled poured onto ice-water (150 ml) the mixture extracted with ethyl acetate (150 ml The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml) dried (Na2SO4) evaporated to dryness under reduced pressure the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent

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

Procedure: Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malondialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 ml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%). heated to reflux under nitrogen, for 18 h The resultant dark solution was cooled poured onto ice-water (150 ml) the mixture extracted with ethyl acetate (150 ml The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml) dried (Na2SO4) evaporated to dryness under reduced pressure the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent