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filingDate 1982-08-06-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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publicationDate 1984-02-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber JP-S5927869-A
titleOfInvention Preparation of 4-oxo-4,5,6,7-tetrahydroindole
abstract PURPOSE: To prepare the titled compound useful as a precursor for the synthesis of an antiarrhythmic agent, pindolol, in high efficiency, by using easily available inexpensive 4-oxo-4,5,6,7-tetrahydrobenzofuran as a raw material, and reacting the material with ammonia. n CONSTITUTION: The objective compound of formula III is prepared by (1) reacting chloroacetaldehyde with 1,3-cyclohexanedione of formula I in the presence of a base such as NaHCO 3 , pyridine, etc. in a reaction liquid of 4W10pH, at -10°CW near the room temperature, if necessary adding a binary-phase solvent such as water and ethyl acetate, etc. to the reaction system, (2) treating the reaction product with an acid to obtain the 4-oxo-4,5,6,7-tetrahydrobenzofuran of formula II (R and R' are H or alkyl), and (3) reacting the compound with ammonia and water in a solvent such as ethanol at 130W170°C. n USE: Synthetic intermediate of 4-substituted indole-based pharamaceuticals., etc. n COPYRIGHT: (C)1984,JPO&Japio
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