7-NITRO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-2-YLAMINE synthesis

Yield: 65%

Reaction Conditions:

with ammonium acetate;sodium cyanoborohydride in methanol at 50; for 15 h;

Steps:

174.D
Step D: 7-Nitro-1,2,3,4-tetrahydro-2-naphthalenamine; 7-Nitro-3,4-dihydro-2(1H)-naphthalenone (200 mg, 1.1 mmol) was combined with ammonium acetate (807 mg, 10.5 mmol), sodium cyanoborohydride (86 mg, 1.4 mmol) and MeOH (5 mL) and heated to 50° C. for 15 h. The reaction was cooled and concentrated under vacuum and the residue was partitioned between EtOAc and water. The organic layer was washed with 5% aqueous potassium carbonate, brine and dried over Na₂SO₄. The crude was concentrated under vacuum and purified by silica gel flash column chromatography (0-100% (90% DCM/9% MeOH/1% NH₄OH)/DCM). Purification provided 130 mg (65%) of the desired amine as a brown oil. ¹H NMR (400 MHz, DMSO-d₆) δ 7.90-7.89 (m, 2H), 7.31 (d, J=8.5 Hz, 1H), 3.06-2.88 (m, 3H), 2.84-2.72 (m, 1H), 2.54-2.44 (m, 2H), 1.81 (d, J=35.2 Hz, 2H), 1.51-1.42 (m, 1H).

References:

SmithKline Beecham Corporation US2008/51395, 2008, A1 Location in patent:Page/Page column 105