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A stirred solution of 1-chloro-5/7-nitroisoquinolines (D1, 1.8 g, 8.6 mmole) in DMF (20 ml) was treated with N-methyl piperazine (1.7 g, 17.2 mmole) and heated at 100 for 3 h. After cooling, the solvent was removed in vacuo and the residue partitioned between water and EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to dryness in vacuo. The residue was passed through a silica gel column eluting with DCM/MeOH/NH4OH 19:1:0.1 giving the title compounds as a red oil (1.2 g, 51%). MS: m/z (MH+) = 273.
A stirred solution of a mixture of 5- and 7-nitroisoquinolin-1-ols (Chem. Pharm. Bull. 1968, 16, 715; 3.8 g, 20 mmole) in POCl3 (15 ml) under argon was heated under reflux for 3 h. After cooling the POCl3 was removed in vacuo and the residue partitioned between DCM and saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to dryness in vacuo giving the title compounds as a pale yellow solid (3.7 g, 89%). MS: m/z (MH+) = 209.
With hydrogenchloride In water; butan-1-ol at 90℃;
4.2.6. General procedure for synthesis of Intermediate 7
General procedure: 4.2.6. General procedure for synthesis of Intermediate 7; A mixture of 1-chloro-7-nitroisoquinoline (100 mg, 0.48 mmol), aniline derivatives (0.72 mmol) and 50 lL concd HCl in n-BuOH(3 mL) was stirred at 90 C overnight. The mixture was poured into ice-water, extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4, concentrated to afford the desired product as a solid which was used without further purification.