Water → 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine

6-Bromo-3,4-dihydro-2H-naphthalen-1-one (9.5 g, 42.2 mmol) was suspended in 2-propanol (250 ml); then, NaBH3 CN (13.3 g, 211 mmol) was added, followed by ammonium acetate (65.1 g, 844 mmol). The reaction mixture was then stirred at RT for 4 hours. It was subsequently heated up to reflux and stirring was continued for 22 hours. The reaction mixture was then cooled down to RT and poured into cold H2O (500 ml); the pH was adjusted to >10 with sodium hydroxide solution and the mixture was extracted with CH2Cl2 (2×25 ml). The organic layers were dried over MgSO4, filtered and concentrated in vacuo to give a crude product (9.842 g) which was purified by flash chromatography (silica gel, 100 g, 2% to 10% MeOH in CH2Cl2) to yield the title compound (8.08 g, 85%) as light red oil. MS: 226.0 (MH+, 1Br).

1. temperatureIt was subsequently heated up
2. temperatureto reflux
3. stirringstirring
4. waitwas continued for 22 hours
5. temperatureThe reaction mixture was then cooled down to RT
6. extractionthe mixture was extracted with CH2Cl2 (2×25 ml)
7. dry with materialThe organic layers were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a crude product (9.842 g) which
11. customwas purified by flash chromatography (silica gel, 100 g, 2% to 10% MeOH in CH2Cl2)

ORD record

ord-04c80125912645e39f13a1f977dea0c8

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592426B2