3-Chloroisoquinoline

A mixture of 1, 3-dichloroisoquinoline (5.00 g, 25.2 mmol), red phosphorus, (1.72 g, 55.5 mmol), and hydriodic acid (10.5 mL, 58.1 mmol) in acetic acid (25 mL) was heated to reflux for 24 hours. The reaction mixture was cooled and poured onto ice, and the resulting solution brought to pΗ 7 by the addition of ION aqueous sodium hydroxide. The solution was extracted with dichloromethane (2 x 50 mL), and the organic layers concentrated. The residue was purified by silica gel chromatography (elution with 10percentEtOAc/hexanes) to provide 1.01 g (24percent) of the title compound. MS (DCIZNHA mixture of 1, 3-dichloroisoquinoline (5.00 g, 25.2 mmol), red phosphorus, (1.72 g, 55.5 mmol), and hydriodic acid (10.5 mL, 58.1 mmol) in acetic acid (25 mL) was heated to reflux for 24 hours. The reaction mixture was cooled and poured onto ice, and the resulting solution brought to pΗ 7 by the addition of ION aqueous sodium hydroxide. The solution was extracted with dichloromethane (2 x 50 mL), and the organic layers concentrated. The residue was purified by silica gel chromatography (elution with 10percentEtOAc/hexanes) to provide 1.01 g (24percent) of the title compound. MS (DCIZNHEXAMPLE 60C General procedure: PdClSynthesis 4-1 -A 3-Chloroisoquinoline 3-Aminoisoquinoline (1.44 g, 10 mmol) was suspended in 10M HCI (5 mL) and cooled to 0°C. Sodium nitrite (689 mg, 10 mmol) was added in portions over 5 minutes. The reaction mixture was stirred at 0°C for 2 hours and allowed to warm to room temperature over 1 hour. The reaction mixture was added carefully to saturated NaHCOA mixture of

Molecular Weight:163.60
XLogP3:3.1
Hydrogen Bond Acceptor Count:1
Exact Mass:163.0188769
Monoisotopic Mass:163.0188769
Topological Polar Surface Area:12.9
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes