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Alpha-methylthio-alpha-(2-aminophenyl) acetaldehyde diloweralkyl acetals
| Details |
Inventors: Gassman, Paul G.;
Assignee: The Ohio State University Research Foundation (Columbus, OH)
Primary Examiner: Wyman; Daniel E.
Assistant Examiner: Doll; John J.
Attorney, Agent or Firm: Hueschen; Gordon W.
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. |
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DETAILED DESCRIPTION OF THE INVENTION More specifically, this invention provides an improved process for making azasulfonium salt intermediates which are useful for making indoles which are known and which have a wide variety of known uses.
According to the process of this invention, a primary or secondary aniline or amino-pyridine starting material, both being referred to hereinafter as an aniline, is first reacted with a source of positive halogen to prepare the N-haloaniline.
Many sources of positive halogen are known and can be used to form the N-haloanilines.
Examples of positive halogen sources for this reaction include tert-butyl hypochlorite, N-chloro-succinimide, calcium hypochlorite, sodium hypochlorite, sodium hypobromite, and the like.
The N-chloro anilines are preferred for reasons of availability of reactants to make them and cost of materials, but other positive halogen compounds can be used to make useful N-haloanilines for use in this process.
The essential features of the process comprise: (a) reacting under substantially anhydrous conditions in an organic diluent at a temperature ranging from the Dry-Ice/acetone mixture temperatures (about -78.
degree.
C) to about 20.
degree.
C an N-halo-aniline of the formula ##STR1## wherein R is hydrogen or a hydrocarbon radical free from aliphatic unsaturation containing from 1 to 8 carbon atoms: A denotes chlorine or bromine, but is preferably chlorine: X is --CH.
dbd.
or N.
dbd.
and is in a position ortho, meta or para relative to the --N(R)A group; each of Y and Z is hydrogen or is a substitutent which does not donate electrons more strongly than m-methoxy, m-hydroxy, or a p-acetoxy group, and not more than one of Y and Z, as a substituent, is ortho to the --N(R)A group position on the ring; the --N(R)A group position on the ring having at least one ring carbon atom ortho thereto in an unsubstituted state; with a .
beta.
-carbonyl sulfide compound or a .
beta.
-carbonyl sulfide acetal or ketal compound having a formula selected from the group cnsisting of ##STR2## wherein R
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