Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-08-09
1978-07-18
Wyman, Daniel E.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
2602948C, 2602948E, 2602948G, 26032612R, 26032613R, 260551R, 260551S, 260577, C07C 9140
Patent
active
041015835
ABSTRACT:
Preparing indoles and intermediates therefor by reacting an N-haloaniline with a .beta.-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the .beta.-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an .alpha.-ethyl-.beta.-carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures. The thio-ether-indole and thio-ether indolenine derivatives are useful as intermediates to make the indoles without the thio-ether group. The indoles are known compounds having a wide variety of uses, e.g., in making perfumes, dyes, amino acids, pharmaceuticals, agricultural chemicals and the like. The present application is particularly directed to alpha-methylthio-alpha-(2-aminophenyl) acetaldehyde diloweralkyl acetals.
REFERENCES:
gassman et al., "J. Amer. Chem. Soc.", 95(2), pp. 591-592 (1973).
Doll John J.
Hueschen Gordon W.
The Ohio State University Research Foundation
Wyman Daniel E.
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