Process for preparing indoline-2-carboxylic acids via alpha-hydr

Details Process for preparing indoline-2-carboxylic acids via alpha-hydr Process for preparing indoline-2-carboxylic acids via alpha-hydr

1985-02-11

1986-04-29

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562434, 562438, 562452, 562456, C07D20942

Patent

active

045858799

ABSTRACT:
Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivatives thereof) comprising the following steps: (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:
patent: 4060626 (1977-11-01), Hrstka et al.
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, 1935-1941 (1967).
Stanton et al., Journal of Medicinal Chemistry, 26, 1267-77, 1268 (1983).
Corey et al., Journal of the American Chemical Society, 2476-2488, at 2480 (1970).
D. Hepburn et al., Chem. Abstracts 82:3698h (1975).
S. Malinowski, Roczniki Chemii, 26, 85 (1952).

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