ChemicalBook CAS DataBase List 4-Amino-1,8-naphthalic anhydride

4-Amino-1,8-naphthalic anhydride synthesis

6synthesis methods

Product Name:4-Amino-1,8-naphthalic anhydride
CAS Number:6492-86-0
Molecular formula:C12H7NO3
Molecular Weight:213.19

6-nitro-1H,3H-naphtho[1,8-cd]pyran-1,3-dione

6642-29-1
56 suppliers
$22.00/250mg

6492-86-0
117 suppliers
$75.00/100mg

Yield:6492-86-0 98%

Reaction Conditions:

with palladium on activated charcoal;hydrogen in acetonitrile at 20; under 760.051 Torr;

Steps:

Synthesis of 4-amino-naphthalic anhydride

4-nitro-1,8-naphthalic anhydride (1.26 g, 5.20 mmol) was transferredto a three-necked round bottom flask and dissolved in 165 mL ofacetonitrile until the solid completely dissolved to a brown-red solution.Palladium on activated carbon (0.18 g) was added to a three-neckround bottom flask, which was sealed and evacuated. The solutionstirred under H2 for 72 h at room temperature and under atmosphericpressure. The reaction solution was then filtered, resulting in the crudeproduct, which was a dark yellow solid, as well as the catalyst. Thecrude product was refluxed in 250 mL of acetone and filtered hot. Thisprocess was repeated and the aliquots of acetone combined until all ofthe crude product was dissolved in acetone and the palladium catalysthad been removed via filtration. The acetone solution was then filteredthrough Celite and removed via rotary evaporation to yield the purifiedproduct. (yellow solid, 1.11 g, 98%)1H NMR (400 MHz, d6-DMSO) 6.88 (d, J=8 Hz, 1H), 7.69 (t,J=7 Hz, 1H), 7.79 (s, 2H), 8.19 (d, J=8 Hz, 1H), 8.44 (dd, J=1,7 Hz, 1H), 8.70 (dd, J=1,8 Hz, 1H).

References:

Jolley, Elizabeth A.;Hardebeck, Laura K.E.;Ren, Yi;Adams, Miranda S.;Lewis, Michael;Znosko, Brent M. [Biophysical Chemistry,2018,vol. 239,p. 29 - 37]

81-86-7 Synthesis