Isopropanol → HCID 14149589, compound

Participants

Reaction Conditions

Reaction Steps

A mixture consisting of 16.5 g 2-(2-methyl-4-diethylaminophenylcarbonyl)benzoic acid (94.6 percent active), 11.0 g of 1-(2-methoxyethyl-2-methylindole) (91.8 percent active) and 75.0 ml of acetic anhydride was heated at approximately 70° C. for approximately two and one-half hours. After cooling to ambient temperature, 50.0 ml of isopropyl alcohol was added and the resulting solution was poured into 800.0 ml of 5 percent aqueous ammonium hydroxide solution. The gummy, tar-like solid which formed was dissolved in toluene and the resulting toluene layer was separated from the water layer. The toluene layer was washed with water and evaporated to dryness to obtain a gummy residue. The residue was triturated with hexane. The resulting slurry was filtered and the solid dried to obtain 19.2 g of 3-[1-(2methoxyethyl)-2-methylindol-3-yl]-3-(2-methyl-4-diethylaminophenyl)phthalide (Formula I: R=CH3OC2H4 ; R1 =R2 =CH3 ; R3 =R4 =C 2 H5 ; X=Y=H), a pale pink solid which melted at 145°-148° C. Significant infrared spectrum maxima appeared at 1755 (C=O;s)cm-1 and 1125 (C--O;s)cm-1. The nuclear magnetic resonance spectrum was in accord with the assigned structures. A toluene solution of the product spotted on an acidic clay or a phenolic resin coated paper developed a cyan-colored image.

Provenance & Evidence