ChemicalBook CAS DataBase List 6-Bromonaphthalen-2-amine

6-Bromonaphthalen-2-amine synthesis

9synthesis methods

Product Name:6-Bromonaphthalen-2-amine
CAS Number:7499-66-3
Molecular formula:C10H8BrN
Molecular Weight:222.08

6-Bromo-2-naphthoic acid (5.07g, 20.19mmol) and triethylamine (4.22mL, 3.07g, 30.3mmol) in dry DMF (155mL) were treated with the diphenylphosphoroyl azide (6.55mL, 8.34g, 30.3mmol) followed by stirring at room temperature for 3h. The solution was then treated with water (2OmL) and warming at 1000C for Ih. The solution was cooled in the flask fitted with a short-path distillation head, and the DMF was removed by distillation under a high vacuum. The solid residue was dissolved in EtOAc and washed with a saturated sodium bicarbonate solution. Filtered through celite, the filtrate was washed with water (3x) and brine. Dried over, filtered, and concentrated under vacuum to give 6-Bromonaphthalen-2-amine as a beige solid (4.48g, 100 percent).

15231-91-1 Synthesis

15231-91-1
412 suppliers
$7.00/5g

7499-66-3
223 suppliers
$19.00/1g

Yield:7499-66-3 94%

Reaction Conditions:

with ammonium bisulfite;ammonia;water at 150; for 48 h;

Steps:

6-bromonaphthalen-2-amine (15)6-Bromonaphthalen-2-ol (1.5 g, 6.7 mmol) was heated with ammonium hydroxide (10ml) and ammonium sulfite (3.5 g, 26 mmol) in a seal tube at 150 ⁰C for 48 h. After cooling to room temperature, ethyl acetate was added and organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and evaporated to obtain crude product 15 (1.4 g, Y; 94 %), which was pure enough and can be used directly for next step without further purification. ¹H NMR (CDCl₃): δ 7.84 (IH, br), 7.56 (IH, d, J= 9.6 Hz), 7.43 (2H, m), 6.95 (2H, m), 3.87 (2H, b). Leigh C. Anderson and Donald G. Thomas: Quinoidation of Triaryl Compounds - Hydroxynaphthyldiphenylcarbinols J. Am. Chem. Soc; 65; 1943; 239, 241.

References:

THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA WO2008/124812, 2008, A1 Location in patent:Page/Page column 53

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5773-80-8 Synthesis