1-methyl-5-(3-nitrophenyl)-1H-Tetrazole → 3-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)aniline

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Reaction Steps

1-Methyl-5-(3-nitrophenyl)-tetrazole (28.8 g, 140 mmol) was dissolved in ethyl acetate (430 mL) and methanol (1270 mL). Palladium on carbon (2.7 g, 10 wt %) was added and the mixture was shaken under a hydrogen atmosphere (60 psig) for 1.5 hours. The mixture was filtered, and the filtrate was concentrated under vacuum to give a white solid (24.0 g, 98%). 1H NMR (300 MHz, CDCl3), δ7.21 (dd, J=8, 7 Hz, 1H) 6.99 (s, 1H), 6.90 (d, J=7 Hz, 1H), 6.76 (d, J=8 Hz, 1H), 5.44 (bs, 2H), 4.10 (s, 3H).

Provenance & Evidence