Reduction of indole-2-carboxylic acids to indoline-2-carboxylic

Details Reduction of indole-2-carboxylic acids to indoline-2-carboxylic Reduction of indole-2-carboxylic acids to indoline-2-carboxylic

1983-02-03

1984-11-27

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20908

Patent

active

044852410

ABSTRACT:
Disclosed herein is an efficient and selective reduction of indole-2-carboxylic acids or esters to indoline-2-carboxylic acids using lithium, sodium, or potassium in liquid ammonia. The preferred process uses lithium in liquid ammonia with small amounts of a weak proton donor such as aniline added to the reaction mixture.

REFERENCES:
Sundberg, R. J. et al., The Chemistry of Indoles, pp. 129-131, (1970), Academic Press, N.Y.
Houlihan, W. J., Indoles, Part One, pp. 166-168, (1972) Wiley-Interscience, John Wiley & Sons, Inc., New York.
Krapcho, A. P. et al., American Chem. Soc., 81, 3658-3664, (1959).
Remers, W. A. et al., J. Amer. Chem. Soc., 89, 5513-5514, (1967).
Hudson et al., "The Synthesis and Chemistry of DL-Indoline-2-Carboxylic Acid", Aust. J. Chem., 20, 1935-1941 (1967).
Corey et al., "Studies in Asymmetric Synthesis of .alpha.-Amino Acids", J. Am. Chem. Soc., 92, 2476, 2480 (1970).
Robinson, B., "The Reduction of Indoles and Related Compounds", Chem. Reviews, 69, 785, 785-787 (1969).
Kaiser, E. M., Synthesis, pp. 391-415, 391 and 408-415 (1972).
Remers, et al., J. Org. Chem., 36, 279-284 (1971).
O'Brien, et al., J. Chem. Soc., pp. 4609-4612 (1960).

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