Water → HCID 88636139, compound

Participants

Reaction Steps

As in example 10 but starting with 1 g 4-chloro-3-formyl-8-methoxy-thioflav-3-ene in 1.5 ml DMF. 220 mg hydroxylamine hydrochloride dissolved in 2 ml DMF are added. After 11/2 hours of reflux, the solution is cooled at room temperature before the addition of 20 ml of water. After extraction with CH2Cl2 a gum is obtained which is purified by column chromatography on silicagel using n-hexane/acetone 9:1 as eluant. Pure 4-chloro-3-hydroxyiminomethyl-8-methoxy-thioflav-3-ene is obtained as a yellow solid. TLC (SiO2, n-hexane/acetone 4:1): Rf =0.15.-NMR (90 MHz, CDCl3): δ(ppm)=3.76 (s, 3H, OCH3), 5.5 [s, 1H, H-C(2)], 6.76-7.69 [m, 3H, H-C(5,6,7)], 7.17 [s, 5H, H-C(2',3',4',5',6')], 8.53 [s, 1H, CH=N], 11.4 [s, 1H, OH].-M.p. 190°-203° C. (n-hexane/toluene).

Provenance & Evidence