4-CHLORO-3-METHYLQUINOLINE

(0554) 3-methylquinolin-4-ol (200 mg, 1.25 mmol) was refluxed in POCl3 overnight. It was cooled to room temperature and poured into ice water, neutralized with Na2C03. The precipitation was filtered out and washed with water, dried by pulling air through. Product was obtained as light yellow solid (142 mg, 64%). :H NMR (400 MHz, chloroform-i/) delta 8.03- 7.96 (m, 2H), 7.78 - 7.73 (m, 1H), 7.70 - 7.65 (m, 1H), 7.53 (ddt, J= 8.1, 7.0, 1.1 Hz, 1H), 2.54 (d, J= 1.0 Hz, 3H).4-Chloro-3-methylquinoline (100.0 mg, 0.56 mmol), 2-(4-nitrophenyl)ethan-1-amine hydrochloride (114.0 mg, 0.56 mmol) and DIPEA (492.0 muL, 2.81 mmol) were dissolved in sulforane (2.8 mL) and stirred at 160 for 18 hours. After addition of H2O, the reaction mixture was stirred and extracted with EtOAc. The organic layer was washed with brine, dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by C18 reversed-phase silica gel column chromatography (CH3CN containing 0.1% formic acid:H2O containing 0.1% formic acid) to obtain the yellow solid, N-(4-nitrophenethyl)isoquinolin-1-amine (31.0 mg, 18%).[801][802]LC/MS ESI (+): 308 (M+1)

Molecular Weight:177.63
XLogP3:3.2
Hydrogen Bond Acceptor Count:1
Exact Mass:177.0345270
Monoisotopic Mass:177.0345270
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes