[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[C:12]#[N:13])=[CH:5][C:4]=1[CH3:14].[CH2:15](N)[CH2:16][NH2:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>[NH:13]1[CH2:15][CH2:16][N:17]=[C:12]1[CH:9]1[C:10]2[C:6](=[CH:5][C:4]([CH3:14])=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1
A mixture of 2.4 grams (0.013 mole) of 6-methoxy-5-methylindanecarbonitrile (iv) and 11.2 grams (0.045 mole) of the ethylenediamine salt of p-toluenesulfonic acid was stirred and heated to about 140° C.-160° C. where it was maintained for about 4.5 hours. The reaction mixture was then cooled to ambient temperature and dissolved in a mixture of aqueous 5% potassium carbonate and methylene chloride. The organic layer was removed, and the aqueous layer was extracted with two portions of methylene chloride. The combined extracts and organic layer were washed with one portion of aqueous 5% potassium carbonate. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a solid residue. The residue was purified by column chromatography on Grade II basic alumina (3% water) using mixtures of methylene chloride and methanol as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding about 2.1 grams of subject compound. The NMR spectrum was consistent with the proposed structure.
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