Ammonia → HCID 53851274, compound

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Reaction Steps

To 35 ml of ammonia were added sodium (50.4 mg, 2.19 mmol) and iron nitride nonahydrate (a catalytic amount) at -78° C. in an argon atmosphere. The mixture was stirred for 15 minutes, while the temperature was allowed to rise. Then, the temperature was returned to -78° C., followed by dropwise addition of a solution of the compound (509 mg, 1.37 mmol) prepared in Example 4 in ether (4 ml). After stirring at the same temperature for 40 minutes, sodium (189 mg, 8.20 mmol) was again added, and the mixture was stirred for a further 30 minutes at the same temperature. Next, ammonium chloride (3.5 g) and ethanol (3.5 ml) were added, followed by heating of the mixture. Ammonia was removed by evaporation, insoluble matters were removed by filtration, and the mixture was washed with ethyl acetate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate 4/1) to obtain 304 mg (yield 83%) of the title compound as a colorless crystals.

Provenance & Evidence