Preparation of 1H-pyrrol-2-acetic acid esters

Details Preparation of 1H-pyrrol-2-acetic acid esters Preparation of 1H-pyrrol-2-acetic acid esters

1984-02-02

1985-01-15

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D207337

Patent

active

044939353

ABSTRACT:
A process for the preparation of esters of 1H-pyrrol-2-acetic acids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R.sub.2 is selected from the group consisting of alkyl of 1 to 4 carbon atoms and aralkyl of 1 to 4 alkyl carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of --CN and ##STR3## in an aqueous media with a saponification base wherein the saponification base is added gradually to the 1H-pyrrol-2-acetonitrile and/or 1H-pyrrol-2-acetamide to selectively saponify the same to obtain a substantially isomer-free salt of 1H-pyrrol-2-acetic acid, adding alkali metal bicarbonate to the solution to keep the pH of solution at about 10.2 to 10.5 and reacting the salt of 1H-pyrrol-2-acetic acid without isolation and without removal of any water with a solution of an alkylating or aralkylating agent in an organic water-insoluble solvent in the presence of a phase transfer agent to obtain the ester of formula I in excellent yields and purity.

REFERENCES:
patent: 3544589 (1970-12-01), Orth et al.
patent: 4255335 (1981-03-01), Carson
Dehmlow, et al., "Phase Transfer Catalysis", (1980), pp. 69-77, (Monographs in Modern Chemistry, vol. 11).
Organic Synthesis, vol. 60, (1981), p. 69.
Organic Synthesis, vol. 55, (1976), pp. 91 and 96.
CRC Handbook of Chemistry & Physics, 61st, ed., (1980), Weast-Editor, CRC Press, Inc., Boca Raton, Florida.

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