Water → HCID 19919517, compound

Participants

Reaction Steps

1.85 g (5.13 mmole) of 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (prepared as described in Example 18) were dissolved in a mixture of 20 ml of acetic acid and 2 ml of acetic anhydride, and then 1.85 g of iron powder were added to the solution, whilst stirring at room temperature; the mixture was then stirred at the same temperature for 90 minutes. At the end of this time, water and chloroform were added to the reaction mixture, and the mixture was neutralized with sodium carbonate. The inorganic salt thus precipitated was filtered off, the remaining organic layer was separated and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was then subjected to silica gel column chromatography, using a 6:4 by volume mixture of toluene and ethyl acetate as the eluent, to give 1.86 g of the title compound. This was crystallized from diisopropyl ether to obtain 1.37 g of the title compound as white crystals, melting at 155°-159° C.

Provenance & Evidence