Preparation of indoline-2-carboxylic acid via the intermediate i

Details Preparation of indoline-2-carboxylic acid via the intermediate i Preparation of indoline-2-carboxylic acid via the intermediate i

1983-02-03

1985-08-13

Hollrah, Glennon H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548491, C07D20918

Patent

active

045351686

ABSTRACT:
Disclosed herein is a process for preparing indoline-2-carboxylic acids from the corresponding indole-2-carboxylic acid or ester in which the indole-2-carboxylic acid or ester is first reduced to the indoline-2-carboxylic acid ester tin complex using stannous chloride and dry hydrogen chloride gas in a lower alkanol solvent at atmospheric pressures; and the resulting tin complex, dissolved in a lower alkanol, is converted directly to the free indoline-2-carboxylic acid by treatment with aqueous potassium or sodium hydroxide. The aqueous hydroxide treatment may take place in situ or after first isolating the intermediate indoline-2-carboxylic acid ester tin complex.

REFERENCES:
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).
Elderfield, R. C., ed., Heterocyclic Compounds, vol. 3, pp. 46-51, (John Wiley & Sons, Inc., New York, 1952).

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