Stannous chloride dihydrate → HCID 67271472, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-amino-1,2-dihydroisoquinolin-3(4H)-one (4.00 g, 20.1 mmol) in 2M HCl (40 mL) at −10° C. was added solid NaNO2 (1.39 g, 20.1 mmol) causing all solids to dissolve. The mixture was stirred at −10° C. for 30 min and then solid SnCl2.2H2O (9.09 g, 40.3 mmol) was added at −10° C. The mixture was allowed to warm to RT over a period of 30 min and then stirred for 2 h. Ethanol (160 mL) and pivaloylacetonitrile (2.52 g, 20.1 mmol) were added and the solution was heated at reflux overnight under Ar atm. The EtOH was removed under reduced pressure, H2O (200 mL) was added, and the mixture was extracted with CH2Cl2 (3×200 mL), dried (MgSO4), concentrated and purified via column chromatography to yield 6-(3-t-butyl-5-amino-1H-pyrazol-1-yl)-1,2-dihydroisoquinolin-3(4H)-one (1.98 g, 35% yield). 1H NMR (400 MHz, CDCl3): δ 7.82 (brs, 1H), 7.40 (brs, 1H), 7.35 (dd, J=8.4, and 2.4 Hz, 1H), 6.80 (d, J=8.8 Hz, 1H), 5.52 (s, 1H), 3.67 (brs, 2H), 3.01 (t, J=7.8 Hz, 2H), 2.65 (t, J=7.4 Hz, 2H), 1.30 (s, 9H); MS (ESI) m/z: 285.2 (M+H+).

Provenance & Evidence