Ammonium Chloride → N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-amino-dibenzo[b,d]furan-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

Third, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide was prepared by reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (prepared using the procedure of Example 4) with zinc. In particular, to a 250 mL 2-necked round bottom flask was added N′-(3,5-dichloropyrid-4-yl)-4-difluoro methoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (1.00 g, 2.14 mmol), sat.aq. ammonium chloride (30.0 mL), ethanol (10.0 mL) and zinc (0.84 g, 12.82 mmol). The reaction mixture was heated to 95° C. over the weekend. The solvent was removed in vacuo, DMF (14 mL) was added to the residue and heated to 50-55° C. until dissolution. The hot solution was filtered, washed with DMF (4 mL) and poured onto water (100 mL). The precipitate was filtered, washed with water (20 mL) and dried in a vacuum oven to yield the amine as a pale yellow solid (0.73 g, 79.4%). Purity 86.31% by HPLC.

Provenance & Evidence