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Chemistry
Organic Building Blocks
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1-Amino-2-(Hydroxymethyl)anthracene-9,10-dione
Chemistry
Organic Building Blocks
Aryls
Amines Alcohols Ketones

[ CAS No. 24094-44-8 ] {[proInfo.proName]}

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Chemical Structure| 24094-44-8
Chemical Structure| 24094-44-8
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CAS No. :24094-44-8 MDL No. :MFCD00168668
Formula : C15H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 253.25 Pubchem ID :-
Synonyms :

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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

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[ 24094-44-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 50-00-0 ]
  • [ 82-45-1 ]
  • [ 24094-44-8 ]
YieldReaction ConditionsOperation in experiment
65% With sodium dithionite; sodium hydroxide In ethanol; water at 60℃; for 0.0111111h; Inert atmosphere; 1-Amino-2-hydroxymethyl-9,10-dioxo-9,10-dihydroanthracene (5) Sodium dithionite (2.26 g, 13 mmol) was added under argon to a suspension of finely powdered 1-amino-9,10-dioxo-9,10-dihydroanthracene (3) (2.20 g, 10 mmol) in 75 mL of a mixture of ethanol:water:1N NaOH (5:1:1.5, v/v/v). The mixture was then heated at 60 °C until a clear light orange solution was obtained, then it was cooled down to rt followed by the addition of 37 % formaldehyde (8 mL, 100 mmol) under argon with vigorous stirring. The reaction was stopped after 40 s and a stream of air was introduced to the reaction mixture from an air-line. The resulting precipitate was collected by filtration, washed with water and dried under vacuum. Column chromatography of the crude product on silica gel using a gradient of acetone/dichloromethane from 1 % up to 5 % gave compound 5 (1.65 g, 65.0 %) as a red solid; m.p. 197 - 199 °C (lit. m.p. 200 - 201 °C) [1]. HPLC-UV (254 nm) ESI-MS, purity: 96.0 %. LC-MS (m/z): 252 [M - H]-, 254 [M + H]+. 1H NMR (500 MHz, DMSO-d6): δ 4.56 (d, 2H, -CH2, 3J 5.45 Hz), 5.47 (t, 1H, -OH, 3J 5.45 Hz), 7.48 (d, 1H, 4-H, 3J3,4 7.5 Hz), 7.63 (d, 1H, 3-H, 3J3,4 7.5 Hz), 7.84 (td, 1H, 6-H or 7-H, 3J5,6 = 3J6,7 = 3J7,8 7.6 Hz, 4J5,7 = 4J6,8 1.4 Hz), 7.89 (td, 1H, 6-H or 7-H, 3J5,6 = 3J6,7 = 3J7,8 7.6 Hz, 4J5,7 = 4J6,8 1.4 Hz), 8.14 (ddd, 1H, 5-H or 8-H, 3J5,6 = 3J7,8 7.6 Hz, 4J5,7 = 4J6,8 1.4 Hz, 5J5,8 0.45 Hz), 8.22 (ddd, 1H, 5-H or 8-H, 3J5,6 = 3J7,8 7.6 Hz, 4J5,7 = 4J6,8 1.4 Hz, 5J5,8 0.45 Hz). 13C NMR (126 MHz, DMSO): δ 60.3 (CH2), 111.6 (C-9a), 115.5 (C-4), 126.2, 126.4 (C-5, C-8), 132.1 (C-3), 132.4, 132.6, 134.5 (C-8a, C-10a, C-4a), 133.4, 134.3 (C-6, C-7), 134.9, 149.6 (C-1, C-2), 182.7 (C-10), 184.4 (C-9). HRMS (ESI-TOF) m/z: [M - H]- calcd. for C15H10NO3 252.0661, found 252.0681.
Reference： [1]Malik, Enas M.; Baqi, Younis; Müller, Christa E. [Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 2326 - 2333]

Tags: 24094-44-8; 1-Amino-2-(Hydroxymethyl)anthracene-9,10-dione; Amines

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