4-Amino-1,8-naphthalic anhydride

4-azido-1, 8-naphthalene anhydride (1.8 g, 7.6 mmol) was dissolved in 100 mL acetonitrile, Sodium sulphide (6.5 g, 41 mmol) was added. Heat to 60°C for 10h, cool, pour into ice water, It was suction filtered and dried in vacuo to give a yellow solid 1.3 g, yield 80percent.General procedure: The synthesis is similar to 1. The residue was purified by columnchromatography on silica gel (eluent: CH2Cl2/CH3OH, 50:1, V/V) togive a yellow solid. Yield: 0.17 g, 79percent. 1H NMR (500 MHz, DMSO) d 8.69 (d, J 8.4 Hz, 1H, ePhH), 8.43 (d, J 7.3 Hz, 1H, ePhH), 8.18(d, J 8.4 Hz, 1H, ePhH), 7.79 (s, 2H, eNH2), 7.69 (t, J 7.8 Hz, 1H, ePhH), 6.88 (d, J 8.5 Hz, 1H, ePhH).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, 98percent)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).10 g of compound 3 was placed in 50 mL of absolute ethanol, 40 g of stannous chloride, 50 mL of concentrated hydrochloric acid solution having a mass fraction of 37percent70 reflux 2h, TLC monitoring of raw materials disappeared, cooled to room temperature, pumping, with ice ethanol and anhydrousEther 80mL each washing filter cake, the filter cake into a vacuum dryer to dry, that reddish brown compound 4, the yield of 85percentTo a mixture of Tin dichloride dehydrate (30 g, 0.13 mol) and con. hydrochloric acid (30 g) was added dropwise a suspension of 2a (6.3 g, 0.026 mol) in ethanol (200 ml) with stirring while maintaining gentle reflux. The reaction mixture was allowed to reflux for another 3 hrs.  The mixture was concentrated to 50 ml and poured into 500 ml of distilled water slowly. The resulting precipitate was collected by filtration and washed with 1 percent aqueous NaOH (30 ml × 2) and distilled water (30 ml × 2). The filter cake was dried in vacuum and recrystallized in nitrobenzene to afford the compound 2b (3.4 g, 62 percent, Mp>300 ºC).To a stirred solution of 4-nitro-1, 8-napthalic anhydride(16.4 mmol, 4.0 g) in ethanol (30 mL) was added the solution of SnCl

Molecular Weight:213.19
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:213.042593085
Monoisotopic Mass:213.042593085
Topological Polar Surface Area:69.4
Heavy Atom Count:16
Complexity:341
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes