Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate

Step C. A mixture of ethyl-4-hydroxy-7-methoxyquinoline-3-carboxylate DK-I-39-1 (37.1 g, 150.0 mmol), N, N- dimethylformamide (0.5 mL, 6.5 mmol), and dichloromethane (150 mL) was heated to 35-40 Ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate (0.68 g, 2.75 mmol) was added tophosphorus oxychloride (2 mL) and heated at 140 oc for an hour. The mixture was thenpoured onto ice, neutralized with 1M NaOH resulting in a solid that was filtered, washed withwater and dried to afforded product (0.50 g, 68percent) as yellowish solid. OH (400 MHz; CDCb)1.46 (3H, t, J =4.0 Hz), 3.99 (3H, s), 4.48 (2H, q, J =8.0 Hz), 7.33(1H, m), 7.44 (1H, d, J=2.8 Hz), 8.30 (1H, d, J= 8.0 Hz), 9.17 (1H, s). 8c (100 MHz; CDCb) 14.2, 55.8, 61.8, 107.6, 120.7, 121.5, 126.7, 143.4, 150.9, 151.7.Description 106; Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate; A suspension of Description 105 (28. 6 g, 0.12 mol) in POCl3 (34 ml, 0.36 moD was heated at 115°C for 45mins. The cooled reaction mixture was poured onto ice (500 ml) and cooled in an ice bath. 33percent aqueous ammonia was added until a pH of 7 was obtained (80-90 ml). The solid which formed was collected by filtration. Ether was added to the solid, the mixture stirred then filtered. This procedure was repeated 4 times and the combined ether extracts were evaporated to give a yellow solid (ll. lg, 36percent). 1H NMR (400 MHz, DMSO-d6) 1.38 (3 H, t, J7. 1), 3.99 (3 H, s), 4.41 (2 H, q, J7.1), 7.48 (1 H, dd, J9. 3 and 2. 6), 7.53 (1 H, d, J2.5), 8. 28 (lH, d, J9.2), 9.10 (1 H, s).

Molecular Weight:265.69
XLogP3:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:265.0505709
Monoisotopic Mass:265.0505709
Topological Polar Surface Area:48.4
Heavy Atom Count:18
Complexity:300
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes