Sodium Hydroxide → HCID 22310859, compound

Participants

Reaction Steps

A solution of ethyl N-(3,4-dichlorobenzyl)-4-nitroindole-2-carboxylate (2.41 g) in tetrahydrofuran (100 ml) was stirred in the presence of titanium trichloride (15% aqueous solution, 50 ml) at room temperature overnight. The reaction was treated with 40% sodium hydroxide solution and extracted with 5% methanol in dichloromethane. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the product as a brown solid (1.98 g, 89%); NMR d (CD3SOCD3) 1.3 (t, 3H), 4.2 (q, 2H), 5.7 (s, 4H), 6.2 (d, 1H), 6.6 (d, 1H), 7.0 (m, 1H), 7.25 (m, 1H), 7.5 (d, 1H), 7.6 (m, 1H): M/z (+) 363.3 (MH+).

Provenance & Evidence