Ethanone, 1-(2,3-dihydro-5-nitro-1H-indol-1-yl)- → 1-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one

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Reaction Steps

Palladium on carbon (10%, 1.110 g) is added to a mixture of N-acetyl-5-nitro indoline (II, EXAMPLE 1, 5.00 g) in ethyl acetate (freshly opened bottle, about 500 ml). The mixture is stirred under 1 atm of hydrogen (ballon) for 39 hr then filtered and the palladium on carbon is washed with methanol/ethyl acetate (20/80). The filtrate is concentrated under reduced pressure to give the title compound, mp 183°-185°; NMR (CDCl3, 300 MHz) 8.01, 6.53, 6.50, 3.98, 3.56, 3.04 and 2.17 δ; CMR (CDCl3 ; 75.47 MHz) 23.86, 28.05, 48.71, 111.55, 113.73, 117.66, 132.8, 135.6, 149.1 and 168.1 δ; IR (CHCl3, 3000, 1640, 1600, 1490, 1410, 1330 and 1300 cm-1.

Provenance & Evidence