1-aminonaphthalene-2-carboxylic acid Chemical Properties

Melting point:

205-206℃

Boiling point:

378.5±30.0 °C(Predicted)

Density 

1.352±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

5.02±0.10(Predicted)

Appearance

Yellow to brown Solid

1-aminonaphthalene-2-carboxylic acid Usage And Synthesis

Synthesis Reference(s)

Journal of Medicinal Chemistry, 37, p. 745, 1994 DOI: 10.1021/jm00032a007

Synthesis

General procedure for the synthesis of 1-amino-2-naphthalenecarboxylic acid from 1-nitro-2-naphthalenecarboxylic acid: 1-nitro-2-naphthalenecarboxylic acid (17.3 g), acetic acid (2 g), and a Pd/C catalyst (1.83 g, 10 wt% Pd) were suspended in THF (339 mL) in reactor A. The reaction was carried out in the same manner as the reaction. The reaction mixture was degassed and pressurized with hydrogen (25 psig). The mixture was stirred and reacted for 10 hours under hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth (6 g) and the filter cake was washed with THF (51 mL). The combined filtrates were concentrated to about 40 mL and then cooled at 0-5 °C. Water (143 mL) was added to the concentrate to induce crystallization of the product. 1-Amino-2-naphthalenecarboxylic acid was isolated by filtration, washed with water (100 mL), and dried to give 13.35 g of product in 92.2% yield, 99.5% liquid phase purity (LCAP), and 98.7% wt. purity.

References

[1] Patent: WO2017/58691, 2017, A1. Location in patent: Page/Page column 13
[2] Chemische Berichte, 1918, vol. 51, p. 1243