Fischer indole synthesis distilling

Fermentation, 22, 53 Ferric nitrate, 23, 20 Fieser s solution, 21, 110 Filter fabric, Pyrex glass, 22, 33, 65 Vinyon, 22, 33, 67 Filter paper, hardened, 22, 45 Fischer indole synthesis, 22, 98 Flash distillation, 21, 85 Flask, modified Claisen, 22, 11 Fluorescence of 9-aminoacridine hydrochloride, 22, 7 Formaldehyde, 20, 60 Formalin, 22, 66 Formic acid, 20, 66, 102 23, 43 Formic acid, chloro-, benzyl ester, 23, 13... 

Filter paper, hardened, 22, 45 Shark skin, 25, 97 Fischer indole synthesis, 22, 98 Flash distillation, 21, 85 Flask, modified Claisen, 22,11 Fluorescence of 9-aminoacridine hydrochloride, 22, 7... 

General procedure for the one-pot Fischer Indole synthesis To allow comparison of the data, a procedure similar to that described in ref. [5] was used. The catalyst (3.00 g) was suspended into a solution of 1 -phenyl-2-butanone (1.48 g, 10.0 mmoles) in p-xylene (30 g). The mixture was then heated to reflux, and after 15 minutes phenylhydrazine (1.08 g, 10 mmoles) was added in one portion. Samples were taken at regular intervals and analyzed by GC using a CP Sil-5 CB capillary column. In several cases, the indole isomer mixture was isolated from the reaction mixture by vacuum distillation after removal of the catalyst and the solvent. NMR shift values and coupling constants for 4 and 5 were identical to those reported in ref. 

Experiment. E. Fischer s Indole Synthesis.—Mix 2 g. of phenylhydrazine with 2 c.c. of acetone in a test tube. Water is eliminated and a turbidity appears. Suspend the tube in the boiling water bath for forty-five minutes, then add 6 g. of dry zinc chloride and heat the mixture for a few minutes with stirring in an oil bath at 180°. Now wash the dark-coloured melt into a small round-bottomed flask with four volumes of dilute hydrochloric acid and separate the resultant a-methylindole by distillation with steam. The substance collects as an oil which soon solidifies. After drying crystallise it from a little petrol ether. Melting point 59°. 

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