Diethylamine → HCID 58112801, compound

Participants

Reaction Steps

To a solution of 5-(chloromethyl)salicylaldehyde (14)(345 mg, 2 mmol) in acetonitrile (70 mL), diethylamine (0.21 mL, 2 mmol) was added and the mixture refluxed overnight. Then, the solvent was evaporated to give compound 15 (625 mg, 99%) as a yellow oil. □max 3383, 2648 and 1653 cm−1. 1H-NMR δH 1.37 (6H, t, J=7.2 Hz, 2×CH2CH3), 3.43 (4H, q, J=7.2 Hz, 2×CH2CH3), 4.09 (2H, s, CCH2N), 7.05 (1H, d, J=8.6 Hz, HAr), 8.03 (1H, d, J=8.6 Hz, HAr), 8.14 (1H, s, HAr), 9.98 (1H, s, CHO), 12.32 (1H, br s, OH). 13C-NMR δC 11.4, 46.4, 56.0, 118.8, 121.3, 136.7, 139.0, 162.7, 196.5. m/z(ESI) 208 (MH+, 100), 293 (30), 317 (10). HRMS (ESI): Calculated for M+ (C12H17NO2+) 208.1338. Found 208.1355.

Provenance & Evidence