Aluminium lithium hydride → 10-(hydroxymethyl)-6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-one

Participants

Reaction Steps

Fine powder of methyl 5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline-10-carboxylate (11.3 g, 28.8 mmol) was suspended in THF (150 mL) and stirred at room temperature. A 2M solution of Lithium aluminium hydride (LAH) in THF (39 mL) was added slowly to the stirred suspension. After the complete addition, the mixture was stirred at room temperature for 6 hours, then cooled to 0° C. The reaction mixture was quenched with dropwise addition of ethyl acetate (50 mL). During the quenching the reaction temperature was kept below 50° C. The reaction mixture was poured into 1N HCl solution (200 mL) and stirred for 1 hour. The resultant solid was collected by filtration, washed with 1N HCl solution (20 mL) and ethyl acetate, and dried in a vacuum oven overnight to provide 10-hydroxymethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline in 93% yield (9.5 g). 1H NMR spectrum (in DMSO-d6): δ 12.28 (s, 1H); 8.23 (d, J=8.1 Hz, 1H); 7.89 (m, 1H); 7.73 (m, 2H); 7.45 (m, 1H); 7.36 (m, 2H); 5.22 (d, J=5.1 Hz, 1H), 4.68 (d, 2H); 3.85 (s, 2H).

Provenance & Evidence