Malonic Acid → HCID 54191491, compound

Participants

Reaction Conditions

Reaction Steps

Piperidine (0.1 ml) was added to a stirred, homogeneous mixture of 3-(1-tridecynyl)pyridine-4-carboxaldehyde (0.73 g, 2.56 mmole, from Example 1), malonic acid (523 mg, 5.12 mmole) and pyridine (5 ml) under nitrogen and the mixture was heated to 80° C. for 1 hour. After then refluxing for an additional 3 hours the mixture was cooled, added to water (40 ml) and acidified to pH 1. The resulting precipitate was washed with water, dried and recrystallised from methanol to give 0.48 g (57%) of the title compound, mp 177°-178° C., νmax (mull) 2450 (broad), 1870 (broad), 1690, 1625, 1595 cm-1 ; δ(DMSO) 0.84 (3H, distorted t, terminal CH3), 1.23 (14H, m, alkylene chain), 1.45 (2H, m, CH2 (CH2)2C≡C), 1.59 (2H, m, CH2CH2C≡C), 2.54 (2H, t, J 6.6 Hz, CH2C≡C), 6.88 (1H, d, J 16 Hz, C=CHCO), 7.82 (1H, d, J 5 Hz, C-5H), 7.83 (1H, d, J 16 Hz, Ar CH=C), 8.52 (1H, d, J 5 Hz, C-6H), 8.64 (1H, s, C-2H), 12.81 (1H, s, OH).

Provenance & Evidence