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Quality Control of [ 7575-82-8 ] Purity: 95+% SDS Specification

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Product Details of [ 7575-82-8 ]

CAS No. :	7575-82-8
Formula :	C₁₀H₁₅NO₂
M.W :	181.23
SMILES Code :	O=[N+](C12CC3CC(C2)CC(C3)C1)[O-]
English Name :	1-Nitroadamantane
MDL No. :	MFCD01321099

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Application In Synthesis of [ 7575-82-8 ]

* 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.

Downstream synthetic route of [ 7575-82-8 ]

[ 7575-82-8 ] Synthesis Path-Downstream 1~8

1
[ 281-23-2 ]
[ 768-92-3 ]
[ 58652-35-0 ]
[ 768-95-6 ]
[ 7575-82-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 74% 2: 10.7% 3: 9% 4: 3.7%	With nitronium tetrafluoborate In various solvent(s) Ambient temperature; Further byproducts given;
1: 3.7% 2: 10.7% 3: 9% 4: 74%	With nitronium tetrafluoborate In various solvent(s) Ambient temperature; Further byproducts given;
	With nitronium tetrafluoborate; water 1.) nitromethane, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

References: [1]Olah, George A.; Ramaiah, Pichika; Rao, Chandra B.; Sandford, Graham; Golam, Rasul; Trivedi, Nirupam J.; Olah, Judith A. [Journal of the American Chemical Society, 1993, vol. 115, # 16, p. 7246 - 7249].
[2]Olah, George A.; Ramaiah, Pichika; Rao, Chandra B.; Sandford, Graham; Golam, Rasul; Trivedi, Nirupam J.; Olah, Judith A. [Journal of the American Chemical Society, 1993, vol. 115, # 16, p. 7246 - 7249].
[3]Olah, George A.; Ramaiah, Pichika; Rao, Chandra B.; Sandford, Graham; Golam, Rasul; Trivedi, Nirupam J.; Olah, Judith A. [Journal of the American Chemical Society, 1993, vol. 115, # 16, p. 7246 - 7249].

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[ 7575-82-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Nitrogen dioxide; ozone at -78 - 30℃; for 0.5h;	1 Example 1: An amantadine hydrochloride, as shown in Figure 1, includes the following weight components: 5mmol of nitro compound, 5g of catalyst, 15ml of absolute ethanol, 15ml of concentrated hydrochloric acid, 15ml of hydrazine hydrate and 3ml of sodium hydroxide solution. The preparation method of the nitro compound includes the following steps: S201: Put adamantane and nitrogen dioxide into a 250ml flask and stir at 30 °C; S202: Pass in nitrogen dioxide at -78 °C and pass in ozone at low speed to react for 30 minutes; S203: Add sodium bicarbonate solution after the reaction, separate layers, and wash the organic phase to neutral; S204: After drying with anhydrous sodium sulfate, the product is obtained by rotary evaporation. The adamantane is 1.092 g, and the nitrogen dioxide is 120 ml. The preparation method of the catalyst includes the following steps: S301: Put ethanol and ether into a 250mL round bottom flask, and quickly put 1.5g FeCl3·6H2O; S302: After pulverizing the FeCl3·6H2O solid by electromagnetic stirring, add activated carbon and continue stirring for 2 hours; S303: Rotary evaporation to remove the solvent, and dry at 100 °C to obtain a catalyst. The ethanol is 10 mL, the ether is 50 mL, and the activated carbon is 5 g. A preparation method of amantadine hydrochloride includes the following steps: S101: Add the nitro compound, absolute ethanol and catalyst to a 50 mL flask respectively; S102: Heat to 40 °C in a nitrogen environment, and slowly drop hydrazine hydrate with a concentration of 85%; S103: After the reaction is completed, the crude product of amantadine is obtained through filtration and rotary evaporation; S104: Add 15 mL of concentrated hydrochloric acid to the crude amantadine product, and stir for 0.5 h at 70 °C; S105: After extracting with dichloromethane, take the hydrochloric acid layer; S106: Filter and dry to obtain pure amantadine hydrochloride. When this example is used, the yield of nitro compounds is 90%, the conversion rate of nitro compounds catalytically reduced by hydrazine hydrate is 98.5%, and the yield of amantadine hydrochloride obtained is 89.5%. The production process of hydrazine hydrate catalytic reduction method has no pollution, high yield, and mild reaction conditions. The catalysts used include precious metal catalysts, iron compound catalysts and zeolite catalysts. Compared with the iron compound catalyst, the cost is lower, and it has a good catalytic effect, and the reaction conditions are mild, the equipment requirements are simple, and the conversion rate is high.
83%		10 Example 10 The conversion of adamantane was 83% and the yield of the nitroadamantane was 72%.
79%	With N-hydroxyphthalimide; nitric acid; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 10h;

72%		36 Example 36 Example 36 The reaction was effected in the same manner as Example 32 except for using managanese acetate Mn(Oac)2instead of Mn(AA)2. The conversion of adamantane was 77%, and nitroadamantane (yield 72%) was formed.
66%	With N-hydroxyphthalimide; air; Nitrogen dioxide In various solvent(s) at 70℃; for 14h;
63%	With trifluoromethylsulfonic anhydride; tetrabutylammonium nitrate In nitromethane for 144h; Ambient temperature;
	With Nitrogen dioxide; ozone In dichloromethane for 0.5h;	2-3 C1: Synthesis of nitro compounds; C11: Add adamantane and dichloromethane into the flask at a ratio of 1g:120ml, and stir at a certain temperature; C12: Pass 30 equivalents of nitrogen dioxide under certain conditions, C13: Pass in ozone at low speed and react for 30 minutes; C14: Then add sodium bicarbonate solution, then wash the organic phase to neutral, C15: Rotary steaming after drying can obtain the product 1-nitroadamantane;
93 %	With Nitrogen dioxide at 70℃; Supercritical conditions; Autoclave;	General procedure for nitration. General procedure: A 22 cm3 steel autoclave with a magnetic stirrer and sapphire windows was loaded with the substrate (and oxygen, if needed), filled with CO2 in a third and cooled down to 10 °C in a thermostat. The calculated amount of cooled to 0 °C NO2 was loaded into a separate cylinder and dissolved in liquid CO2 (3-5 cm3). The obtained solution was warmed up to room temperature and added to the autoclave by capillary with valve due to the pressure difference between the warm cylinder and the cooled autoclave. The residual NO2 was transferred from the cylinder to the autoclave with fresh CO2 until the latter was filled by ~3/4 volume. Then the autoclave with the reaction mixture was kept at the required temperature for the planned time. If UV irradiation was needed, the autoclave was equipped with photodiodes (375-380 nm, two pieces of 3 W) in front of the sapphire windows. After completion of the reaction, the autoclave was cooled to room temperature and carefully decompressed via the outlet valve releasing gaseous CO2 and keeping the reaction products at the bottom of the autoclave. The purification of the products 2, 3, 6a,b was performed by column chromatography (silica gel, n-hexane).

References: [1]Current Patent Assignee: TIANJIN MINXIANG PHARMACEUTICAL - CN112500296, 2021, A Location in patent: Paragraph 0044-0051.
[2]Current Patent Assignee: DAICEL CHEMICAL INDUSTRIES - EP897747, 1999, A1.
[3]Koguchi, Shinichi; Kitazume, Tomoya [Tetrahedron Letters, 2006, vol. 47, # 16, p. 2797 - 2801].
[4]Current Patent Assignee: DAICEL CHEMICAL INDUSTRIES - EP897747, 1999, A1.
[5]Sakaguchi, Satoshi; Nishiwaki, Yoshiki; Kitamura, Takaaki; Ishii, Yasutaka [Angewandte Chemie - International Edition, 2001, vol. 40, # 1, p. 222 - 224][Angewandte Chemie, 2001, vol. 113, p. 228 - 230].
[6]Duddu, Rajagopal; Damavarapu, Reddy [Synthetic Communications, 1996, vol. 26, # 18, p. 3495 - 3501].
[7]Current Patent Assignee: TIANJIN MINXIANG PHARMACEUTICAL - CN112479896, 2021, A Location in patent: Paragraph 0070-0077; 0090-0097.
[8]Budkova, Alexandra V.; Merkulov, Vladislav G.; Ivanov, Roman E.; Zharkov, Mikhail N.; Kuchurov, Ilya V.; Zlotin, Sergei G. [Mendeleev Communications, 2023, vol. 33, # 4, p. 461 - 462].

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[ 7575-82-8 ]
[ 100-59-4 ]
[ 33187-62-1 ]