2-Amino-6-bromonaphthalene

Preparation of 6-bromonaphthalen-2 -amine.; [00748] A solution of the product Part A (5.07g, 20.19mmol) and triethylamine (4.22mL, 3.07g, 30.3mmol) in dry DMF (155mL) was 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) followed by warming at 100[00490] Part B. Preparation of 6-bromonaphthalen-2-amine.; [00491] A solution of the product Part A (5.07g, 20.19mmol) and triethylamine (4.22mL, 3.07g, 30.3mmol) in dry DMF (155mL) was 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) followed by warming at 100Part 1. Preparation of 6-bromonaphthalen-2 -amine.[00328| A solution of the product Part H (5.07 g, 20.19 mmol) and triethylamine (4.22 mL, 3.07 g, 30.3 mmol) in dry N.N-dimethylformamide (155mL) was treated with the diphenylphosphoroyl azide(6.55 mL, 8.34 g, 30.3 mmol) followed by stirring at room temperature for 3 hours. The solution was then treated with water (20 mL) followed by warming at 100 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 Preparation of 6-Bromonaphthalen-2-amine (9) General procedure: Ammonium hydroxide aqueous solution ( 841mg, 27.8 mmol, 2 equiv.) was added to a freshly prepared aqueous solution of ammonium sulfite monohydrate (3.2 g, 27.8 mmol, 2 equiv.) in a 35 ml high pressure reaction vessel. Appropriate 2-naphthol analog (1a or 1b) (13.9 mmol, 1 equiv.) was added, and the mixture was stirred for 17 h at 120 °C. The reaction mixture was filtered and the precipitate was washed with cold 5percent aq. NaOH and then dissolved in DCM. The organic layer was again washed with 5percent aq. NaOH (3×30 mL) and dried over anh. sodium sulfate to afford 2-naphthylamines after the removal of solvent in vacuo.General Procedure VII-SA flask was charged with VII-IB (5.5 g, 17.1 mmol) and HCl/MeOH (4M, 170 mL) was stirred at room temperature for 4 hrs. After the completion of reaction, the mixture was concentrated to afford 6-bromonaphthalen-2-amine (VII-Vd) (2.5 g, yield 66percent).

Used in the new synthesis of alkylsulphanylnaphthalenes and the synthesis and mesomorphic properties of novel naphthylisothiocyanates.

Molecular Weight:222.08
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:220.98401
Monoisotopic Mass:220.98401
Topological Polar Surface Area:26
Heavy Atom Count:12
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes