Methylamine → 4-(1-Naphthyl)-2,2-dimethyl-7-(3-methylamino-2-hydroxy-propoxy)-2H chromene

Participants

Reaction Steps

Methylamine (9.5 ml) was added to 7-(2,3-epoxypropoxy)-2,2-dimethyl-4-(1-naphthyl)-2H chromene (4.5g., 0.013 moles) in ethanol (9.5ml) and the solution left to stand at room temperature for 48 hours. Removal of solvent gave the title compound as an orange oil (3.2g., 63%). N.M.R. (τCDCl3) 8.54(s, 3H, CH3 --), 8.48(s, 3H, CH3 --), 7.06(s, 3H, N--CH3), 6.72(d, 2H, --CHCH2 --), 6.05(d, 2H, --CH2CH--), 4.51(s, 1H, vinylic CH), 3.40-3.80 (m, 3H, aromatic H's), 2.10-2.75(m, 7H, aromatic H's).

Provenance & Evidence