Potassium Nitrate → 4-methyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one
Reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][CH2:3]1.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-methyl-3,4-dihydro-2H-isoquinolin-1-one (1. Og) (J. Med. Chem., 1988, 31, 433) in conc. sulfuric acid (5 ml) was added dropwise over 20 min to an ice cooled solution of potassium nitrate (0.678 g) in conc. sulfuric acid (5 ml). The mixture was stirred for a further 30 min with ice-cooling. The mixture was added dropwise to ice (150 g) with stirring. The precipitated solid was collected by filtration, washed with water and dried to give the sub-titl compound (0.95 g). 1H NMR δ: 1.28 (3H, d, J=6.6 Hz), 3.14-3.28 (1H, m), 3.52 (2H, m), 7.67 (1H, d, J=8.5 Hz), 8.29 (1H, s), 8.35 (1H, dd, J=2.5, 8.4 Hz) (1H, d, J=2.5 Hz).