Sodium Hydroxide → HCID 57733369, compound

Participants

Reaction Steps

3-Methyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester (4.2 g, 13.7 mmol) was dissolved in 100 ml of hot methanol and a solution of NaOH (6 g) in water (20 ml) was added. The reaction mixture was heated at reflux for 2 hrs, diluted with water (200 ml) and stirred overnight at ambient temperature. Organic volatiles were removed under reduced pressure and the obtained aqueous solution was extracted with ethyl acetate (2×50 ml). The aqueous solution was poured into ice/2M HCl (150 ml). The obtained suspension was sonicated, and the product was separated by filtration, washed with water and dried in vacuo to give 2.9 g of a colourless solid, yield 76%. LC-MS (m/z) 280.2 (MH+); tR=0.9. 1H NMR (500 MHz, DMSO-d6): 2.01 (s, 3H), 7.36 (d, 2H), 7.50 (t, 1H), 7.56 (q (overlapping m), 3H), 7.72 (d, 1H), 7.81 (t, 1H), 8.22 (d, 1H), 13.5 (br, 1H).

Provenance & Evidence