2-Naphthaleneethanamine

General procedure: Step 2: Preparation of Intermediate 2-(4-Chloro-phenyl)-ethylamine (I-1b) 1-Chloro-4-(2-nitro-vinyl)-benzene (I-1a: 3.4 g, 0.0185 mmol) dissolved in dry THF (50 mL) was added dropwise to a stirred suspension of LAH (1.3 g, 0.03707 mmol) in dry THF (50 mL) over a period of 20 minutes at 0 C. under nitrogen atmosphere. The resulting mixture was stirred at 45 C. for 3 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was cooled to room temperature, quenched with 10% NaOH solution (3 mL), and filtered through Celite bed. The filtrate was washed with ethylacetate and concentrated under reduced pressure to afford 2.6 g of the crude product which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz): delta 7.49-7.00 (m, 6H), 2.9 (t, 2H), 2.6 (t, 2H)General procedure: To a cooled (0C) solution of 2-methoxy-3-(2-nitrovinyl)naphthalene (1.49 g, 6.49 mmol) in anh. THF (10mL) is added dropwise a solution of lithium aluminum hydride (2 M in THF, 11.4 mL, 22.8 mmol). Themixture is then heated at reflux (80C), under nitrogen, for 15 mm. The cooled (0C) RM is treated successively with water (0.9 mL), 15% aq. NaOH (0.9 mL), and water (2.6 mL). The resulting heterogeneous mixture is then filtered and the separated solid is washed with Et20. The layers of the filtrate are separated and the aqueous layer is extracted with Et20. The combined organic layers are then dried over anh. MgSO4, filtered and concentrated under reduced pressure affording 2-(3-methoxynaphthalen-2-yl)ethan-1-amine as a yellow oil (1.30 g, 99%). LC-MS A: tR = 0.58 mm; [M+H] = 202.20.

Molecular Weight:171.24
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:171.104799419
Monoisotopic Mass:171.104799419
Topological Polar Surface Area:26
Heavy Atom Count:13
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes