Water → Indoline-4-ol

Participants

Reaction Steps

A solution of 4-hydroxyindole (0.16 g; 1.2 mmol) in AcOH (6 ml) was treated with NaBH3CN (0.23 g; 3.6 mmol), at rate keeping the temperature below 15° C. The mixture was then stirred for 1 h at room temperature and H2O (0.4 ml) was added and solvents removed in vacuo. The residue was diluted to 15 ml with EtOAc, washed with 5% NaHCO3, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated under reduced pressure to give the title compound (0.16 g; 99%) as creamy solid. 1H-NMR (CDCl3) 2.93 (tr, 2H, J=8.4 Hz); 3.58 (tr, 2H, J=8.4 Hz); 3.74 (broad s, 2H); 6.17 (d, 1H, J=8 Hz); 6.26 (d, 1H, J=7.72 Hz); 6.88 (tr, 1H, J=7.85 Hz).

Provenance & Evidence