Methyl Salicylate → HCID 9892423, compound

Participants

Reaction Conditions

Reaction Steps

Methyl salicylate (78 mmol) was mixed with distilled TREN (17 mmol). The mixture was sealed and heated to 100° C. overnight. The thick resulting oil was purified on a silica column eluted with 0-4% MeOH in CH2Cl2, resulting in a white powder after removal of solvent. Overnight drying in vacuo gave a colorless glass. Yield: 47%. IR (KBr) 1543, 1590, 1636 cm31 1. 1H NMR(300 MHz, CD3OD, 25 C) 2.78 (t, 3J=6.2 Hz, 6H, CH2), 3.49 (t, 3J=6.2 Hz, 6H, CH2), 6.68 (t, 3J=7.2 Hz, 3H, ArH), 6.80 (d, 3J=7.4 Hz, 3H, ArH), 7.23 (t, 3J=5.8 Hz, 3H, ArH), 7.63 (d, 3J=6.4 Hz, 3H, ArH), 8.44 (t br, 3H, NH). 13C NMR (400 MHz, CD3OD, 25 C) 39.0 (CH2), 54.6 (CH2), 117.1 (Ar), 118.4 (Ar), 120.2 (Ar), 129.0 (Ar), 134.7 (Ar), 160.9 (ArCO), 170.9 (C═O). Anal. Calcd (Found) for C27H30N4O6: C, 64.02 (63.94); H, 5.97 (5.97); N, 11.06 (11.01).

Provenance & Evidence