6-Chloro-3-methylisoquinoline

During 10 min. (4-chloro-benzyl)-[2, 2-dimethoxy-1-methyl-eth-(Z)-ylidene]-amine (120 g, 0.496 mol) was added dropwise to polyphosphoric acid (1000 g) at 130 During 10 min. (4-chloro-benzyl)-[2, 2-dimethoxy-1-methyl-eth-(Z)-ylidene]-amine (120 g, 0.496 mol) was added dropwise to polyphosphoric acid (1000 g) at 130 J3. 3-Bromomethyl-6-chloro-isoquinoline 6-Chloro-3-methyl-isoquinoline (750 mg, 4.22 mmol) was dissolved in 1, 2-dichloroethane (70 mL). To this solution was added N-bromosuccinimide (901 mg, 5.07 mmol) and azobisisobutyronitrile (69 mg, 0.42 mmol). The reaction was heated at reflux for 5 hrs. The reaction was diluted with DCM, brine was added and the layers were separated. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. Flash column chromatography eluting with petroleum ethenethyl acetate afforded 3-bromomethyl-6-chloro-isoquinoline (980 mg, 90% yleld). [MH]+ = 255/257J2. 6-Chloro-3-methyl-isoquinoline (4-Chloro-benzyl)-(2, 2-dimethoxy-1-methyl-ethyl)-amine (1.25 g, 16.55 mmol) was added dropwise to chlorosulphonic acid (100 mL) at -10 C over a period of 10 min. The reaction mixture was then stirred at 100 C for 10 min after which time the reaction mixture was cooled and poured into ice and neutralised (to pH7) with 33% isiaOH. Care was taken that temperature did not rise above 35 C. The reaction mixture was extracted with chloroform (3 x 100 mL). The combined organics were washed with water (100 mL), brine (100 mL), dried (Na2SO4) and filtered and evaporated in vacuo. The residue was purified by flash chromatography (silica), eluent 3% MeOH, 97% chloroform to give 6-chloro-3-methyl- isoquinoline (750 mg, 82% yleld)

Molecular Weight:177.63
XLogP3:3.3
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