ChemicalBook CAS DataBase List 2-Chloro-1,4-naphthoquinone

2-Chloro-1,4-naphthoquinone synthesis

11synthesis methods

Product Name:2-Chloro-1,4-naphthoquinone
CAS Number:1010-60-2
Molecular formula:C10H5ClO2
Molecular Weight:192.6

83-72-7
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$14.14/1gm:

1010-60-2
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$5.00/5g

Yield:1010-60-2 85%

Reaction Conditions:

with thionyl chloride at 90; for 48 h;

Steps:

2-chloronaphthalene-1,4-dione (11)
A solution of Lawsone (870 mg, 5 mmol, 1 equiv) in thionyl chloride (25 mL) was stirred at 90 °C for 48 h. After cooling, the mixture reaction was verted in water (200 mL). The precipitated compound was filtered, taken up with chloroform (100 mL), washed with solution of sodium bicarbonate10% in water (100 mL). The organic layer was dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel with hexane/ethyl acetate (13:1) to afford the desired product as yellow solid (816 mg, 4.25 mmol, 85%), mp 93-95 °C; 1H NMR (400 MHz,CDCl3) δ 8.21-8.15 (m, 1H), 8.12-8.06 (m, 1H), 7.83-7.75 (m, 2H),7.23 (s, 1H); 13C NMR (101 MHz, CDCl3) δ 182.8, 178.1, 146.4, 136.0,134.6, 134.3, 131.8, 131.4, 127.6, 126.9. The spectral data are in accordance with those reported in the literature [36].

References:

Calil, Felipe A.;David, Juliana S.;Chiappetta, Estela R.C.;Fumagalli, Fernando;Mello, Rodrigo B.;Leite, Franco H.A.;Castilho, Marcelo S.;Emery, Flavio S.;Nonato, M.Cristina [European Journal of Medicinal Chemistry,2019,vol. 167,p. 357 - 366]

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