ChemicalBook CAS DataBase List 6-(DiMethylaMino)-2-naphthoic acid

6-(DiMethylaMino)-2-naphthoic acid synthesis

11synthesis methods

Product Name:6-(DiMethylaMino)-2-naphthoic acid
CAS Number:5043-05-0
Molecular formula:C13H13NO2
Molecular Weight:215.25

50-00-0 Synthesis

50-00-0
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5043-05-0
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Yield:5043-05-0 100%

Reaction Conditions:

with sodium cyanoborohydride in methanol;water at 20; for 0.5 h;

Steps:

1

To a solution of 6-amino-2-naphthoic acid (1) (Sigma-Aldrich Japan KK) (90%, 3.00 g, 14.4 mmol) in methanol (120 ml) was added sodium cyanotrihydroborate (3.63 g, 57.7 mmol) and formaldehyde (37% in water, 24 ml), and the reaction mixture was stirred at room temperature for 30 min. After evaporation of the solvent, the residue was extracted with water and chloroform. The aqueous layer was acidified to pH 1 with HCl to give a yellow-ochre solid, and extracted with chloroform. The organic layer was washed with brine, dried over Na₂SO₄, filtered and evaporated in vacuo to yield compound (2) (3.23 g, quant.) as a yellow-ochre solid; ¹H NMR (DMSO-d₆) δ 12.63 (brs, 1H), 8.36 (d, 1H, J=1.5 Hz), 7.88 (d, 1H, J=9.2 Hz), 7.78 (dd, 1H, J=1.8, 8.6 Hz), 7.66 (d, 1H, J=9.0 Hz), 7.26 (dd, 1H, J=2.6, 9.2 Hz), 6.94 (d, 1H, J=2.6 Hz), 3.04 (s, 6H); MS (EI) m/z 215 [M⁺]; HRMS (EI) calculated for C₁₃H₁₃O₂N [M⁺] 215.0946, found 215.0946.

References:

US2006/142311,2006,A1 Location in patent:Page/Page column 18; sheet 2

67-56-1 Synthesis