2-Naphthalenecarboxaldehyde → HCID 67936478, compound

Participants

Reaction Steps

To a mixture of 2-naphthaldehyde (4.69 g, 30 mmol) and beta-anilinopropionitrile (4.82 g, 33 mmol) in dimethyl sulfoxide (35 ml) was added potassium t-butoxide (3.70 g, 33 mmol). The solution immediately turned a dark red. It was heated at 100° for 30 minutes, cooled, and diluted with methanol (15 ml) and water (25 ml). A copious yellow precipitate formed, which was chilled and isolated. The precipitate, 2-(2-naphthylmethyl)-3-anilinoacrylonitrile, was washed with dilute methanol and hexane; yield, 7.65 g. A portion was recrystallized from absolute ethanol; m.p. 148°-153° C. Anal. Calcd. for C20H16H2 : C, 84.48; H, 5.67; N, 9.85. Found: 84.38; H, 5.69; N, 9.82.

Provenance & Evidence