4-(4-methoxyphenyl)butanal

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

Procedure: 4-(4-Methoxyphenyl)butyraldehyde (5.34 g) is reacted with cyanoacetic acid (5.15 g) and sodium hydroxide (2.74 g) in a mixture of glyme (50 ml) and water (60 ml). The mixture is treated with hydrochloric acid and processed as described in Example 2A to afford the title compound (2.1 g) which on crystallization from ethyl acetate-chloroform-hexane had a melting point of 71°-73° C.

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

Procedure: 4(4-Methoxyphenyl)butyraldehyde (5.34 g) is reacted with cyanoacetic acid (5.15 g) and sodium hydroxide (2.74 g) in a mixture of glyme (50 ml) and water (60 ml). The mixture is treated with hydrochloric acid and processed as described in Example 2A to afford the title compound (2.1 g) which on crystallization from ethyl acetate-chloroform-hexane had a melting point of 71°-73° C.

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

Procedure: 4-(4-Methoxyphenyl)butyraldehyde (5.34 g) is reacted with cyanoacetic acid (5.15 g) and sodium hydroxide (2.74 g) in a mixture of glyme (50 ml) and water (60 ml). The mixture is treated with hydrochloric acid and processed as described in Example 2A to afford the title compound (2.1 g) which on crystallization from ethyl acetate-chloroform-hexane had a melting point of 71°-73° C.

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

Procedure: 4(4-Methoxyphenyl)butyraldehyde (5.34 g) is reacted with cyanoacetic acid (5.15 g) and sodium hydroxide (2.74 g) in a mixture of glyme (50 ml) and water (60 ml). The mixture is treated with hydrochloric acid and processed as described in Example 2A to afford the title compound (2.1 g) which on crystallization from ethyl acetate-chloroform-hexane had a melting point of 71°-73° C.

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

Procedure: 4-(4-Methoxyphenyl)butyraldehyde (5.34 g) is reacted with cyanoacetic acid (5.15 g) and sodium hydroxide (2.74 g) in a mixture of glyme (50 ml) and water (60 ml). The mixture is treated with hydrochloric acid and processed as described in Example 2A to afford the title compound (2.1 g) which on crystallization from ethyl acetate-chloroform-hexane had a melting point of 71°-73° C.

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

Procedure: To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-(piperidin-2-yl-methoxy)-1H-quinolin-2-one (prepared essentially as described in Example 10, 34 mg in 3.0 mL dry methanol) was added 18 mg of 4-(4-methoxyphenyl)-butyraldehyde, 150 mg powdered 4 Å molecular sieves and one drop of acetic acid. After 30 minutes, 0.13 mL of a 1M solution of sodium cyanoborohydride in tetrahydrofuran was added and the mixture stirred at room temperature for 18 hours. At this time the reaction mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo. Purification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3) gave the title compound, 39 mg. At this time the reaction mixture was filtered through diatomaceous earth the filtrate concentrated in vacuo Purification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3)

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

Procedure: 4(4-Methoxyphenyl)butyraldehyde (5.34 g) is reacted with cyanoacetic acid (5.15 g) and sodium hydroxide (2.74 g) in a mixture of glyme (50 ml) and water (60 ml). The mixture is treated with hydrochloric acid and processed as described in Example 2A to afford the title compound (2.1 g) which on crystallization from ethyl acetate-chloroform-hexane had a melting point of 71°-73° C.