Cyanoacetic acid → HCID 24694331, compound

Participants

Reaction Steps

3,4,5-Trimethoxyaniline (10.00 g, 54.6 mmol) and cyanoacetic acid (4.78 g, 56.19 mmol) were mixed in 100 mL of tetrahydrofuran and heated to reflux. To the resultant solution 1,3-diisopropylcarbodiimide (8.8 mL, 56.29 mmol) was added dropwise. The mixture was cooled in an ice-bath and the solid was collected by filtration washing with tetrahydrofuran. The filtrate was slowly poured into water and stirred for 30 minutes. The white solid was collected by filtration, washed with water and dried to give 2.58 g of 2-cyano-N-(3,4,5-trimethoxyphenyl)acetamide as a white solid, mp 146-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.61 (s, 3H), 3.74 (s, 6H), 3.86 (s, 2H), 6.90 (s, 2H), 10.23 (s, 1H); MS (ES) m/z251.1 (M+H)+

Provenance & Evidence