Ethyl 5-nitro-3indolepropionate → 5-Nitro-3-(3-hydroxypropyl)-1H-indole

Participants

Reaction Steps

To a suspension of 95% LiAlH4 (2.20 g, 0.058 mol) in 60 mL of dry THF was added a solution of ethyl 5-nitro-3-indolepropionate (7.30 g, 0.028 mol) in 100 mL of dry THF, at 0° C. under Ar. After stirring for 20 min, the mixture was quenched by the cautious addition of 3 mL of H2O. The resulting suspension was stirred for 10 min and then it was filtered and the filtercake was washed with additional THF. The filtrate was evaporated and the residue was taken up in ether, dried (Na2SO4) and evaporated, and the resulting solid was triturated with hexane to give the title compound (4.30 g, 70%) as a yellow solid, mp 107°-110° C.: IR (KBr) 3480, 3180, 1625 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ8.60 (d, J=2.1 Hz, 1H), 8.35 (br s, 1H), 8.11 (dd, J=9.0, 2.2 Hz, 1H), 7.38 (d, J=8.9 Hz, 1H), 7.16 (m, 1H), 3.75 (t, J=6.2 Hz, 2H), 2.91 (t, J=7.2 Hz, 2H), 2.07-1.93 (m, 2H), 1.37 (br s, 1H).

Provenance & Evidence