Methanol → 3-Methoxy-3-(1-ethyl-2-methylindol-3-yl)phthalide

Participants

Reaction Steps

Proceeding in a manner similar to that described in Example 1 above, 5.1 g of 2-(1-ethyl-2-methylindol-3-yl)carbonylbenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of pyridine to obtain 2.1 g of 3-methoxy-3-(1-ethyl-2-methylindol-3-yl)phthalide (Formula III: R0 =R=R1 =R2 =R8 =H; R6 =C2H5 ; R7 =Y=CH3 ; X=O), a dark brown-colored oil. Significant infrared maxima appeared at 1770 (C=O;s) and 740 cm-1 (C=O;s). Analysis by mass spectrum showed m/e peaks at 321 (M+) and 290 (M+ --OCH3). A toluene solution of the product spotted on an acidic clay-coated paper developed a red-purple-colored image.

Provenance & Evidence