Aminocarboxylic Acids

Abstract

Aliphatic aminocarboxylic acid are prepd. by a reaction of amino alkyl chlorides with ammonium polysulfide soln. (I) and acidification of the reaction product with mineral acid. Thus, a mixt. of 10.6 g. NH2(CH2)5Cl, 120 cc. I (contg. 2.1 moles H2S and 10.1 moles NH3/l.), 21 g. S, and 80 cc. C5H5N is heated in a steel bomb 6 hrs. at 160°. The mixt. is evapd. to dryness in vacuo on the H2O-bath, and the residue extd. with hot H2O. The ext. is evapd. to dryness, and the residue refluxed 10 hrs. with concd. HCl. The mixt. is evapd. in vacuo on the H2O-bath, and the residue digested with abs. EtOH and filtered. The filtrate is evapd. to dryness to give 3.5 g. δ-amino-n-valeric acid-HCl (II); anilinoformyl deriv., m. 160°. II is also formed in the same manner from AmNH2-HCl, which has been chlorinated to contain 1.1 g. atom Cl. Similarly 20 g. chlorinated BuNH2-HCl contg. 0.98 g. atom Cl is heated 6 hrs. at 160° with 250 cc. I and 40 g. S to yield 6 g. γ-aminobutyric acid-HCl; anilinoformyl deriv., m. 126°. A mixt. of 12 g. chlorinated hexylamine-HCl contg. 1 g. atom Cl, 20 g. S, 80 cc. C5H5N, and 120 cc. I is heated 6 hrs. at 160° and treated as above to yield 3 g. ε-aminocaproic acid-HCl; anilinoformyl deriv., m. 126°. Cf. Ger. 929,192 (C.A. 52, 1240i). [on SciFinder(R)]