Allylamine → 7-(Allylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

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Reaction Steps

To a solution of 7-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile [prepared from commercially available 7-bromo-2-tetralone following a similar procedure as described in WO2004/071389A2](500 mg, 2.9 mmol) in 20 mL of anhydrous DCM was added 3 drops of HOAc, allylamine (330 mg, 5.8 mmol) and NaBH(OAc)3 (2.46 g, 12 mmol), and the mixture was stirred at RT under nitrogen for 48 hours. DCM was added and the mixture was washed with saturated NaCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give 7-(Allylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

Provenance & Evidence