Formaldehyde → 1-Methyl-3-(2-hydroxyethyl)pyrazinium iodide

Participants

Reaction Steps

2.0 g of 2-(2-hydroxyethyl)pyrazine (301) prepared by a known method by condensing formaldehyde and 2-methylpyrazine, was dissolved in 5 ml of methanol and 5 ml of methyl iodide added. The solution was refluxed for 3 days, concentrated and the residue purified by gel permeation chromatography. Freeze-drying gave 3.2 g of yellow solid product (300). It was recrystallized from ethyl acetate/ethanol, m.p. 94°-5°. UV H2O max: 226 (4.13), 281 (3.85). 13C NMR: 163.25, S (C3); 150.71, D (C5); 138.69, D, 136.25, D (C2, C6); 60.38, T (CH2OH); 49.88, Q (NCH3); 38.75, T (--CH2 --). 1H NMR: 9.35, D, T (H6); 8.97, S (H2); 8.85, D (H5); 4.49, S (NCH3); 4.08, T; 3.35, T (ArCH2, CH2OH).

Provenance & Evidence