Water → 1H-Indole-3-ethanamine, 5-nitro-
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][C:14]#[N:15])([O-:3])=[O:2].O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10]([NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][NH2:15])=[CH:11][CH:12]=1)([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dissolve (5-nitro-1H-indol-3-yl)-acetonitrile (9 g, 44.7 mmol) in 250 mL dry THF and treat with 90 mL 1 M BH3 in TBF at ambient temperature. Stir overnight and quench the reaction cautiously by the dropwise addition of 10 mL water. Concentrate to dryness under vacuum and partition the residue between 5 N HCl and EtOAc. Extract the aqueous layer with EtOAc and combine with the original EtOAc layer. Treat the aqueous layer with 5 N NaOH and extract 3 times with 10% MeOH in EtOAc. Purify by flushing the extracts through a pad of 100 g SCX ion exchange resin, rinsing with 2 liters of MeOH which was discarded, and then eluting with the 2 M NH3 in MeOH and concentrating to give the title compound as a dark solid: ISMS 206 (M+1); Analysis for C20H18F6N2O2 0.3H2O 0.1C7H8: calcd: C, 57.34; H, 5.74; N, 19.29; found: C, 57.30; H, 5.38; N, 19.08; 1H NMR (DMSO-d6) 11.9–11.2 (bs, 1H), 8.50–8.49 (d, 1H), 7.95–7.92 (m, 1H), 7.47–7.45 (m, 1H), 7.38 (s, 1H), 2.79 (s, 4H), 2.2–1.3 (bs, 2H).