5-Nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid → 5-Amino-2,3-dihydro-1-benzofuran-7-carboxylic acid

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Reaction Steps

The crude 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid was dissolved in the minimum amount of methanol (1.3 L) and nitrogen was bubbled through the solution for 20 minutes. A mixture of 5% palladium on charcoal (1.0 g) in water (20 ml) was added and the mixture loaded into a 2 L autoclave. After 2 sequential evacuation-N2 purges the vessel was charged to 5 bar H2 and stirred for 4 days. The mixture was flushed with nitrogen, filtered through celite and concentrated to give 5-amino-2,3-dihydrobenzo[b]furan-7-carboxylic acid (3.5 g, 19.5 mmol, 63% over 2 steps)

Provenance & Evidence