Butyronitrile, 4-chloro

Dimethylindole magnesium iodide reacts with chloroacetonitrile in ether to give 3-cyanomethyl-2,3-dimethylindolenine (234). Majima and Hoshino obtained 3-(2-cyanoethyl)lndole (235) by the action of -chloropropionitrile on indole magnesium iodide. The reaction was slower with -chloropropionitrilc than with chloro-aoetonitrile. 3-(3-Cyano-w-propyl)indole (236), required as an intermediate in the synthesis of 3-indolyl-y-w-butyric acid, was prepared, but not isolated, by the action of y-chloro-w-butyronitrile on indole magnesium iodide. ... 

The submitter reports that an equivalent number of moles of Y-bromobutyronitrile or a mixture of 7-chloro- and 7-bromo-butyronitrile may be substituted for 7-chlorobutyronitrile. If the bromo compound is used the reaction mixture should be refluxed six hours and it is necessary to filter off the sodium bromide just before the final vacuum distillation. 

Azido-butyronitrile, N3.CH2.CH2.CHA.CN mw 110.12, N 50.88% liq, bp 55-60° at 5mm was prepd by heating 4-chloro-butyronitrile with NaNs when this compd is treated with chlorosulfbnic acid(ClS03H) in chlf or with coned H2S04 in CCl4 at 20-40°, Trimethylenetetrazole is formed (Refs 1 2)... 

To a hot solution of potassium cyanide (80 gms.) dissolved in 125 gms. of water, hot 96 per cent, alcohol is added (500 c.c,), and to this clear, hot mixture, trimethylene chlorobromide (200 gms.) is added the whole is then boiled for 1 hours on the water-bath under a reflux condenser, The alcohol is next distilled off, and carries with it most of the unchanged trimethylene chlorobromide, Water is then added to the residue in the flask to dissolve potassium salts, and the oily layer is distilled after drying over calcium chloride. After two or three fractionations the portion boiling at 192°—205° is taken as y-chloro-butyronitrile. B.p. 195°—197°. Yield, 50 per cent. 

Trdger s base R,S-2,2,2-Trifluoro-l-(9-anthryl)ethanol ( )-2-(4-chloro-6-methyl-amino-[ 1,3,5]triazin-2-ylamino)-2-methyl-butyronitrile... 

Alkylation of pyrrole magnesium bromide and chloride with y-chloro-butyronitrile gives 2- and 3-cyanopropylpyrrole (2 >3). The isomer distribution is similar to those observed in reactions with butyl chloride, heptyl chloride and 8-methoxybutyl chloride. It is concluded that the constitution of pyrrole magnesium chloride is the same in tetrahydrofuran as in ether s. 

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