2-Methyl-3-quinolinamine

A solution of 2-methyl-3-nitroquinoline (400 mg, 2.13 mmol) in cone. HCI (8 mL) was heated to 50 °C. Tin (II) chloride dihydrate (1 .2 g, 5.3 mmol) was added. The mixture was stirred at 50 °C overnight. The mixture was diluted with water (20 mL). The pH was brought to 9 by addition of aqueous 5 N NaOH. The mixture was cooled to 4 °C and extracted with ethyl acetate (2 x 30 mL). The combined extracts were washed with ice-cold water (40 mL) and dried over anhydrous NaA mixture of 2-aminobenzaldehyde (6.0 g, 49.58 mmol), 1-(2-oxopropyl)pyridinium chloride (8.98 g, 52.06 mmol), pyridine (2.6 ml, 32.72 mmol) and 4-dimethylaminopyridine (60 mg, 0.49 mmol) in ethanol (75 ml) were refluxed for 48 h. The reaction mixture was cooled to room temperature and pyrrolidine (10.3 ml, 123.96 mmol) was added, and mixture was then refluxed for 16 h. The volatiles were removed under reduced pressure and the resultant mixture was diluted with aqueous sodium bicarbonate solution (200 ml). The mixture was extracted with dichloromethane (2 x 200 ml). The combined organic layers were washed with brine (200 ml) and dried over anhydrous sodium sulphate. The organic layer was filtered and concentrated under reduced pressure. The residue obtained was purified by flash silica gel column chromatography to yield 4.8 g of product as a yellow solid.

Molecular Weight:158.20
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:158.084398327
Monoisotopic Mass:158.084398327
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes