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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
50964-11-9

6-AMINO-1H-BENZO[CD]INDOL-2-ONE synthesis

8synthesis methods
6-NITRO-1H-BENZO[CD]INDOL-2-ONE

34599-42-3
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6-AMINO-1H-BENZO[CD]INDOL-2-ONE

50964-11-9
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Yield:50964-11-9 100%

Reaction Conditions:

with hydrogenchloride;tin(ll) chloride in water at 50; for 4 h;

Steps:

6-aminobenzo[cd]indol-2(1H)-one (22)

Compound 21 (171mg, 0.8mmol) was slowly added as a solid under stirring to a solution of SnCl2 (645mg, 3.40mmol) in HCl (37%, 4mL) and water (1.5mL). The reaction mixture was stirred at 50°C for 4h. Then it was cooled to 0°C and basified to pH 10 by adding an aqueous solution of NaOH (6M). The crude was then extracted with ethyl acetate (x3) and the combined organic layers were dried over MgSO4 and concentrated under reduced pressure and filtered through Celite to afford the desired compound (147mg, 0.798mmols, quantitative yield). 1H NMR (400MHz, DMSO-d6) δ (ppm): 10.87 (br s, 1H), 8.32 (d, J=8.2Hz, 1H), 8.09 (d, J=6.9Hz, 1H), 7.91 (dd, J=8.3, 7.0Hz, 1H), 7.41 (d, J=7.4Hz, 1H), 6.97 (d, J=7.5Hz, 1H). 13C NMR (101MHz, DMSO-d6) δ (ppm): 168.6, 137.2, 131.5, 129.4, 127.1, 125.9, 124.8, 123.4, 123.3, 122.2, 105.9; HRMS: (m/z) calcd. for C11H8N2O [M+H]+: 185.0715, found 185.0689.

References:

Quintana, Mireia;Bilbao, Ana;Comas-Barceló, Júlia;Bujons, Jordi;Triola, Gemma [European Journal of Medicinal Chemistry,2019,vol. 178,p. 648 - 666]

130-00-7 Synthesis
Benz[cd]indol-2(1H)-one

130-00-7
235 suppliers
$5.00/5g

6-AMINO-1H-BENZO[CD]INDOL-2-ONE

50964-11-9
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References
2-{2,4-dinitrophenoxy}-6-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione

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6-AMINO-1H-BENZO[CD]INDOL-2-ONE

50964-11-9
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References
2-Hydroxy-6-nitro-benzo[de]isoquinoline-1,3-dione

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6-AMINO-1H-BENZO[CD]INDOL-2-ONE

50964-11-9
14 suppliers
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References
6-nitro-1H,3H-naphtho[1,8-cd]pyran-1,3-dione

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

6-AMINO-1H-BENZO[CD]INDOL-2-ONE

50964-11-9
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References