Hydroxylamine → 6-[amino(hydroxyimino)methyl]-1H-indole-2-carboxylic acid

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Reaction Conditions

Reaction Steps

A solution of 6-cyano-1H-indole-2-carboxylic acid (prepared according to J. Org. Chem. 1953, 18, 345-357, 1 g; 5.37 mmol; 1 eq.), hydroxylamine (50% in water; 1.77 mL; 26.86 mmol; 5 eq.) in EtOH (10 mL) was stirred at RT for 14 hours after which it was further heated at 60° C. for 28 hours. Solvents were removed under vacuum to give the title compound as a white powder (1.227 g; quantitative yield). 1H NMR (DMSO-d6) δ 11.75 (s, 1H), 7.72 (s, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.37 (dd, J=1.2, 8.5 Hz, 1H), 7.00 (d, J=1.2 Hz, 1H), 5.76 (bs, 2H), 3.44 (q, J=7.1 Hz, 2H), 1.05 (t, J=7.1 Hz, 3H).

Provenance & Evidence