Chemical process for the production of racemic spiro- linked...

C - Chemistry – Metallurgy – 07 – D

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260/306.1, 260/3

C07D 487/10 (2006.01) C07D 209/38 (2006.01)

Patent

CA 1209148

ABSTRACT The invention concerns a novel process for the racemisa- tion of unwanted enantiomeric forms of 1'-substituted spiro[imi- dazolidine-4,3'-indoline]-2,2', 5-triones and 1'-substituted spiro[pyrrolidine-3,3'-indoline]-2,2', 5-triones which comprises heating an unwanted enantiomeric form (or a mixture containing an excess of one enantiomer over the other) alone or, more conven- iently, in the presence of a solvent or diluent at a temperature in the range 80 to 280°C. These compounds have the general formula Image wherein Ra is (2-12C)alkyl, or naphthylmethyl or cinnamyl optionally bearing one or two halogeno substituents, or benzyl optionally bearing one or two substituents independently selected from halogen, (1-4C)alkyl, (1-4C)alkoxy, cyano, nitro and tri- fluoromethyl located in the 2-, 3-, 4- or 5-position of the phenyl moiety; benzene ring A optionally bears one or two substituents independently selected from halogeno, (1-4C)alkyl, trifluoromethyl and nitro; and Q is methylene or imino; but Ra is other than ethyl, n-propyl or unsubstituted benzyl when benzene ring A is unsubstituted and Q is imino.

443630

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