Sodium Hydroxide → HCID 56737040, compound

Participants

Reaction Conditions

Reaction Steps

To 5-(4,5-dimethyl-2-nitrophenyl)furan-2-aldehyde (5a) (0.69 g, 2.81 mmol) was added solid NaOH (0.12 g, 3.09 mmol) and 10% NaOH solution (6.2 ml). Silver nitrate (0.47 g, 2.81 mmol) was added, and the reaction mixture heated to 60° C. for 3 h. After cooling to room temperature the resulting mixture was poured into 2N HCl (50 ml) during which the product precipitated out of solution and was collected by filtration. The crude solid was purified by column chromatography using 0-2% MeOH/DCM as eluent. (5i) was obtained yellow solid (41%). mp 231-233° C. 1H NMR (400 MHz, DMSO-d6): δ 2.34 and 2.35 (6H, 2s), 6.93 and 6.94 (dd, J=1.6 and 3.6 Hz, 1H), 7.31 and 7.32 (dd, J=1.2 and 3.2 Hz, 1H) 7.63 (s, 1H), 7.80 (s, 1H) 13.20 (brs, 1H); 13C NMR (100 MHz, DMSO-d6): δ 19.63, 19.84, 111.67, 120.01, 120.63, 125.62, 131.19, 140.48, 143.26, 145.82, 145.91, 152.59, 159.71; HRMS (m/z): [M+H]+ calcd for C13H12NO5, 262.0710; found, 262.0714.

Provenance & Evidence