Acetone →

Participants

Reaction Steps

To estrone nicotinate (0.5 g, 0.0013 mol) in acetone (20 ml) was added methyl iodide (1 ml, 0.016 mol) and the mixture was refluxed overnight. The deep yellow precipitate was filtered, washed with acetone, and dried. Yield 90% (0.6226 g); m.p. 245°-248° C. (dec.). NMR (d5 -DMSO) 9.8-9.7 (br s, 1H, C2 pyridinium proton), 9.4-9.0 (m, 2H, C4, C6 pyridinium protons), 8.4-8.0 (m, 1H, C5 pyridinium proton), 7.4-7.2 (m, 1H, C1 estrone proton), 7.1-6.9 (m, 2H, C2,4 estrone protons), 3.2-1.3 (estrone skeletal protons, 15), 1.0-0.9 (s, 3H, C18 estrone protons). IR (KBr) 1755-1740 (broad C=O stretching). Anal. calculated for C25H28NO3I: C, 58.03; H, 5.47; N, 2.71. Found: C, 58.16; H, 5.51; N, 2.67. The product has the formula: ##STR1487##

Provenance & Evidence