Hydrochloric Acid → 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

This material is commercially available, however, it can be successfully prepared by the following procedure. To a solution of the 6-bromo 2-tetralone (0.288 g, 1.280 mmol) and NH4OAc (0.986 g, 10 eq.) in MeOH (40 mL) is added NaCNBH3 (0.097 g, 1.2 eq) at room temperature. The resulting yellow solution is stirred at that temperature for 20 hours, then acidified with 0.1 M HCl to pH 2.0. The mixture is extracted with CH2Cl2 twice. The aqueous layer is basified with 1.0 N NaOH to pH 10 then extracted with CH2Cl2 three times. The extracts are dried over anhydrous MgSO4 and concentrated in vacuo to afford 0.8 g (44% yield) of the desired product as a yellow oil which is used without further purification. 1H NMR (300 MHz, CD3OD) δ 7.27-7.35 (m, 8H), 7.05 (d, J=8.4 Hz, 4H), 3.56 (m, 1H), 3.17 (dd, J=3.9, 16.2 Hz, 1H), 2.95 (m, 2H), 2.81 (dd, J=9.9, 16.2 Hz, 1H), 2.19-2.29 (m, 1H), 1.79-1.92 (m, 1H); 13C NMR (75 MHz, CD3OD) δ 137.3, 131.5, 131.4, 130.9, 120.1, 47.4, 26.9, 26.7; LRMS: 226.1 (M+H), 209 (M+H−NH3).

1. customhowever, it can be successfully prepared by the following procedure
2. extractionThe mixture is extracted with CH2Cl2 twice
3. extractionthen extracted with CH2Cl2 three times
4. dry with materialThe extracts are dried over anhydrous MgSO4
5. concentrationconcentrated in vacuo

ORD record

ord-de25e0a6c07f49faba21e3d937e55164

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07304065B2