2-(TERT-BUTYL)-6-NITRO-1H-INDOLE synthesis

10synthesis methods

Product Name:2-(TERT-BUTYL)-6-NITRO-1H-INDOLE
CAS Number:873055-09-5
Molecular formula:C12H14N2O2
Molecular Weight:218.25

1H-Indole, 2-(1,1-dimethylethyl)-2,3-dihydro-6-nitro-

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Yield: 80%

Reaction Conditions:

with 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane at 20; for 2.5 h;Heating / reflux;

Steps:

51
To a solution of 2-tert-butyl-6-nitroindoline (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ (6.9 g, 30 mmol) at room temperature. The mixture was heated at reflux for 2.5 h before being filtered and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). ¹H NMR (300 MHz, CDCl₃) δ 8.30 (br. s, 1H), 8.29 (s, 1H), 8.00 (dd, J=2.1, 8.7 Hz, 1H), 7.53 (d, J=9.3 Hz, 1H), 6.38 (s, 1H), 1.43 (s, 9H).

References:

Hadida Ruah, Sara S.;Grootenhuis, Peter D.J.;Van Goor, Frederick;Zhou, Jinglan;Bear, Brian;Miller, Mark T.;McCartney, Jason;Numa, Mehdi Michel Jamel US2007/244159, 2007, A1 Location in patent:Page/Page column 141

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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References

61495-04-3 Synthesis

61495-04-3
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$57.00/1g

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95-53-4 Synthesis

95-53-4
431 suppliers
$10.00/1g

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References

3282-30-2
360 suppliers
$18.00/100ml

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References