Process for preparing indoline-2-carboxylic acids via .alpha.-hy

Details Process for preparing indoline-2-carboxylic acids via .alpha.-hy Process for preparing indoline-2-carboxylic acids via .alpha.-hy

1986-02-14

1987-02-24

Reamer, James H.

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

Organic compounds

Carboxylic acids and salts thereof

C07C101447

Patent

active

046458573

ABSTRACT:
Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivaties thereof) comprising the following step: (a) reducing .alpha.-oxo-2-nitrobenzenepropanoic acid to .alpha.-hydroxy-2-nitrobenzenepropanoic acid, (b) replacing the hydroxyl group of the latter with a chlorine atom utilizing a selected Vilsmeier chlorinating reagent at temperatures of at least 20.degree. C., (c) reducing the nitro group of the resulting .alpha.-chloro-2-nitrobenzenepropanoic acid to obtain .alpha.-chloro-2-aminobenzenepropanoic acid, and (d) cyclizing the latter in aqueous base to form the desired indoline-2-carboxylic acid. Alternately, steps (c) and (d) may be combined in a one pot step by using, for example, a Raney nickel-hydrazine reducing medium.

REFERENCES:
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patent: 3397211 (1968-08-01), Summit
patent: 4060626 (1977-11-01), Hrstka et al.
Corey et al., Journal of the American Chemical Society, 2476-2488, at 2480 (1970).
Malinowski, Roczniki Chemii, 26, 85 (1952).
Hepburn et al., Chem. Abstracts, 82: 3698n (1975).
Houlihan, ed., The Chemistry of Heterocyclic Compounds, vol. 25, part 1, pp. 396-399 (Wiley Interscience, New York 1972).
Hudson, C. B. and Robertson, A. V., Australian Journal of Chemistry 20, 1935-41 (1967).
Stanton et al., Journal of Medicinal Chemistry, 26, 1267-77, 1268 (1983).

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