2-Bromo-4-nitro-naphthalen-1-ylamine synthesis

Yield:63240-26-6 96%

Reaction Conditions:

with N-Bromosuccinimide;ammonium acetate in acetonitrile at 20; for 0.166667 h;

Steps:

2-Bromo-4-nitronaphthalen-1-amine (34)

To a solution of 4-nitronaphthalen-1-amine (1.0 g, 5.31 mmol) in acetonitrile (17 mL) were added ammonium acetate (41 mg, 0.53 mmol) andN-bromosuccinimide(993 mg, 5.58 mmol) at room temperature. The reaction mixture was stirred at room temperature for 10 minutes. After the reaction was completed, the crude mixture was concentrated under reduced pressure, added to water_,and then extracted with ethyl acetate. The organic layer was dried over anhydrousNa₂SO₄andconcentrated under reduced pressure. The resulting solid was dissolved with the minimum amount of dichloromethane, solidified from hexane, and then filtered to give the product as a yellow solid (1.4 g, 96%);¹H NMR (400 MHz,DMSO-d₆)δ8.78 (d,J= 8.8 Hz, 1H), 8.54 (s, 1H), 8.45 (d,J= 8.8 Hz, 1H), 7.79-7.75 (m, 1H), 7.62-7.58 (m, 1H), 7.51 (brs, 2H, NH);¹³C NMR (100 MHz, DMSO-d₆)δ149.5, 132.8, 131.9, 130.3, 126.24, 126.21, 123.7, 123.5, 121.0, 97.6;LC/MS (ESI⁺)m/z267.9 [M(⁷⁹Br) + H]⁺, 269.6 [M(⁸¹Br) + H]⁺.

References:

Abed, Dhulfiqar Ali;Hu, Longqin;Lee, Sumi;Nguyen, Mai-Uyen;Verzi, Michael P. [European Journal of Medicinal Chemistry,2022,vol. 237,art. no. 114380] Location in patent:supporting information