6-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE

To a stirred solution of 2-bromo-5-chlorobenzonitrile (80 g, 370 mmol) in THF (1000 mL) at 0°C was added EtMgBr (370 mL, 1110 mmol) dropwise. The reaction mixture was stilTed at 0-5°C for 5 hours before MeOH (500 mL) was added dropwise. After the solution was stilTed for another 15 mm, NaBH4 (28 g, 740 mmol) was added carefully and the resulting mixture was stirred at room temperature for 16 hours. The reaction solution was then poured into water and exacted with EtOAc (3 x 200 mL). The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crudeproduct, which was purified by column chromatography (petroleum ether: EtOAc =3: 1) to afford the title compound (30 g, 34.6percent) as yellowish oil. MS: 235.5 [M+H’i.Step 1 : 6-chloro-3, 4-dihydroisoquinoline-l(2H)-thione [00243] A mixture of 6-chloro-3, 4-dihydroisoquinolin-l(2H)-one (0.498 g, 2.74 mmol) and phosphorus pentasulfide (0.67 g, 3.0 mmol) in toluene (15 mL) was stirred at 70 C for 21 h. The reaction was cooled to room temperature, filtered through Celite, and concentrated in vacuo. Purification by silica gel chromatography using 2% CH30H/CH2C12 yielded 6-chloro- 3, 4-dihydroisoquinoline-l(2H)-thione (0.48 g, 89.3%) as a yellow solid. 1H NMR (300 MHz, DMSO-de) delta 10.55 (br s, 1H), 8.3 (d, 1H, J = 9 Hz), 7.42 (s, 1H), 7.41 (d, 1H, J = 9 Hz), 3.4 (m, 2H), 2.93 (t, 2H, J = 7 Hz).

Molecular Weight:181.62
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:181.0294416
Monoisotopic Mass:181.0294416
Topological Polar Surface Area:29.1
Heavy Atom Count:12
Complexity:195
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes