Crotalaria rubiginosa Willd, is a shrub native to south India and occurring in other countries of the Orient. An examination has been made of the seed alkaloids of the variety C , rubiginosa Willd. var. wightiana J. G. Baker (syn. C. wightiana R. Grah. ex Wight and Walk.-Am.
suspension was allowed to warm to room temperature over a 5-10min period, diluted with ether, and extracted once each with water, 10% sulfuric acid, saturated sodium bicarbonate, and saturated brine. The dried (MgS04) ethereal solution was evaporated, a 1.4-g crop of yellow crystals (from petroleum ether, bp 60-68°) was separated by filtration, and the concentrated filtrate was distilled under reduced pressure. ¿erí-Butyl thiolbenzoate (8.7 g, 45%) was obtained as a water-white liquid: bp ~135-145°(15-25 mm) [lit.41 bp 127°( 11 mm)]; ir (all s) 687, 772, 908, 1060, 1205, 1655 cm-1 (C=0); nmr 1.55 (s, 9 H), 7.2-7.4 (m, 3 ), 7.7-7. (m, 2 H).A solution of the thiolbenzoate (99 mg, 0.51 mmol) in ~30 ml 50% aqueous dioxane (v/v before mixing) was heated at 105°for 12 days in a sealed ampoule. The ester (83 mg, 84%), recovered by extraction with pentane, had unchanged ir and nmr spectra.
The seed of Crotalaria grahamiana R. Wight & Walk.-Arn.
contains mono- crotaline and a new alkaloid, grahamine, which is a 3?-[(-)-2- methylbutyryl]
derivative of monocrotaline. ��
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