[2-(5-Fluoro-2,4-dinitro-phenyl)-vinyl]-dimethyl-amine → 5-Fluoro-1H-indol-6-amine

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Reaction Steps

A suspension of [2-(5-fluoro-2,4-dinitro-phenyl)-vinyl]-dimethyl-amine (8 g, 31.4 mmol) and Raney Ni (8 g) in EtOH (80 mL) was stirred under H2 (40 psi) at room temperature for 1 h. After filtration, the filtrate was concentrated and the residue was purified by chromatography (Pet.Ether/EtOAc=5/1) to give 5-fluoro-1H-indol-6-ylamine (B-20) as a brown solid (1 g, 16%). 1H NMR (DMSO-d6) δ 10.56 (br s, 1 H), 7.07 (d,J=12 Hz, 1 H), 7.02 (m, 1H), 6.71 (d,J=8 Hz, 1H), 6.17 (s, 1H), 3.91 (br s , 2H); ESI-MS 150.1 m/z (MH+).

Provenance & Evidence