3-Acetonyl-3-hydroxyoxindole
To a well-stirred suspension of 2 mol of isatine (294 g) in acetone (1 L), diethylamine (100 ml) is added in one portion. An exothermic reaction occurs, and the isatine precipitate dissolves within 30 minutes, forming a dark green solution. The solution is stirred for 6 hours, and the precipitate is filtered off. The filtrate is evaporated to dryness in a water bath. The combined residues are washed with a small amount of cold acetone and dried. Tm=167-168 C (with decomposition), yield 85%.
D. 3-hydroxy-3-2'-hydroxynaminopropyl oxindole (oxime of 3-acetonyl-3-hydroxyoxindole)
To 1.6 moles (321 g) of 3-acetonyl-3-hydroxyindole in hot 96% alcohol, add 1.7 moles (118 g) of hydroxylamine hydrochloride dissolved in 1 liter of water and 2.6 moles of sodium acetate (209 g) in 1 liter of water. The solution is kept at room temperature for 1 hour, then evaporated to a small volume in a vacuum over a water bath. The precipitate is filtered off and recrystallized from water. Tm=179-180 C (with decomposition), yield 82%.
E. a-methyltryptamine
0.05 mol (10 g) of 3-acetonyl-3-hydroxyoxindole oxime in 250 mL of THF is added dropwise at room temperature to a well-stirred suspension of 0.28 mol (10 g) of lithium aluminium hydride in 200 mL of THF. The red-brown solution is boiled with a reflux condenser for 12 hours, then cooled, and 40 mL of water is added dropwise. The resulting suspension is filtered and washed with a small amount of ether. The filtrate is evaporated to a small volume in a vacuum on a water bath and extracted with ether. The essential extracts are combined and dried with magnesium sulfate, after which they are distilled in a vacuum (Tbo=137 C at 0.3 mmHg). Tm=226 C, yield 34%.
Please make a video of how the oxime is reduced by sodium in isopropanol. Please, I really need it. I know you can do it)
