8-CHLORO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE

To the mixture of 20 (10.00'g, 45.05'mmol) and ammonium chloride (1.76'g, 32.9'mmol), aluminum chloride (11.60'g, 87.02'mmol) was added at 185'C. After 40'min and 70'min, further portions of aluminum chloride (5.80'g, 43.5'mmol and 11.60'g, 87.02'mmol) were added and the mixture was stirred for further 23'h'at the same temperature. It was poured into a slurry of ice and 3'M HCl solution under strong agitation. The resulting solution was basified (pH 14) with 40% NaOH and extracted with diethyl ether (300'mL and 2?*?150'mL). The organic layer was dried (MgSO4), and evaporated resulting in an oily residue (7.07'g, 94%) containing the two isomers 19 and 27 in a ratio of 9: 1 as determined by GC-MS. It was dissolved in isopropyl alcohol (50'mL) and a solution of hydrochloric acid gas in isopropyl alcohol was added dropwise. The precipitate was filtered off. The residue was recrystallized twice from isopropyl alcohol to afford the title compound (2.32'g, 25%)A one-necked glass flask was charged with 12 (1.20 g, 4.95 mmol, 1.0equiv), 2-methyltetrahydrofuran (10 mL), and MeOH (10 mL), andthen N 2 gas was bubbled through the mixture. Under an inert atmo-sphere, 10% Pd/C (530 mg, 0.5 mmol, 0.1 equiv) was added followed by careful addition of NaBH 4 (206 mg, 5.45 mmol, 1.1 equiv). The flaskwas closed by a gas bubbler filled with silicon oil. The mixture wasstirred for 70 min at 25 C (longer reaction times resulted in an exten-sive formation of over-reduced products such as 1, 2, 3, 4-tetrahy-droisoquinoline and

Molecular Weight:167.63
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:167.0501770
Monoisotopic Mass:167.0501770
Topological Polar Surface Area:12
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes