6588-68-7

Usage

Uses

Used in Pharmaceutical Industry:
3,5-DiMethyl-1-nitroadaMantane is used as a neuroprotective agent for the treatment of neurodegenerative disorders such as Parkinson's disease. Its neuroprotective properties make it a promising candidate for mitigating the progression of these disorders and improving the quality of life for patients.
Used in Neurodegenerative Disorder Treatment:
3,5-DiMethyl-1-nitroadaMantane is used as a therapeutic agent for the treatment of neurodegenerative disorders, particularly Parkinson's disease. It is believed to aid in the protection and preservation of neurons, potentially slowing down the progression of the disease and providing relief from its symptoms.

Synthetic route

1,3-dimethyladamantane (702-79-4) → 1-nitro-3,5-dimethyl-adamantane (6588-68-7)

Conditions	Yield
With N-hydroxyphthalimide; air; Nitrogen dioxide In various solvent(s) at 70℃; under 760 Torr; for 14h;	70%
With nitric acid In neat (no solvent) at 200℃; for 1.5h;	39%
With nitric acid; N-hydroxyphthalimide In various solvent(s) at 60℃; for 15h;

N-hydroxyphthalimide (524-38-9) + 1,3-dimethyladamantane (702-79-4) + α,α,α-trifluorotoluene (98-08-8) → 1-nitro-3,5-dimethyl-adamantane (6588-68-7)

Conditions	Yield
With Nitrogen dioxide	60%

1,3-dimethyladamantane (702-79-4) → 1,3-dimethyl-5-adamantanol (707-37-9) + 1-nitro-3,5-dimethyl-adamantane (6588-68-7)

Conditions	Yield
With nitric acid; acetic acid; [H4PVMo11O40] at 82.85℃; under 760 Torr; Title compound not separated from byproducts;	A 10% B 41 % Chromat.
With nitric acid; acetic acid; [VO(H2O)5]H[PMo12O40] at 82.84℃; Title compound not separated from byproducts.;	A 38 % Chromat. B 56 % Chromat.

1-nitro-3,5-dimethyl-adamantane (6588-68-7) → 3,5-dimethyl-7-nitroadamantan-1-yl nitrate

Conditions	Yield
With nitric acid; acetic anhydride at 10℃; for 3h;	43%

1-nitro-3,5-dimethyl-adamantane (6588-68-7) → memantine hydrochloride (41100-52-1)

Conditions	Yield
Stage #1: 1-nitro-3,5-dimethyl-adamantane With iron; acetic acid at 20℃; for 4.5h; Stage #2: With hydrogenchloride In ethyl acetate for 0.5h;	449.2 g

Upstream product

• 702-79-4 1,3-dimethyladamantane 
• 524-38-9 N-hydroxyphthalimide 
• 98-08-8 α,α,α-trifluorotoluene 

Downstream Products

• 41100-52-1 memantine hydrochloride 

Relevant academic research and scientific papers

Selective Nitroxylation of Adamantane Derivatives in the System Nitric Acid–Acetic Anhydride

Abstract: A number of new nitroxyadamantanes have been synthesized by nitroxylation of the corresponding substrates with nitric acid in acetic anhydride. High electrophilicity and reduced acidity of the system HNO3–Ac2O increases the stability of nitrates and significantly decreases the probability of formation of alcohols. In some cases, nitrolysis and oxidation of functional groups in the substrate are observed.

Nitration of alkanes with nitric acid by vanadium-substituted polyoxometalates

The nitration of alkanes by using nitric acid as a nitrating agent in acetic acid was efficiently promoted by vanadium-substituted Keggin-type phosphomolybdates such as [H4PVMo11O40], [H5PV2Mo10O40], and [H 6PV3Mo9O40] as catalyst precursors. A variety of alkanes including alkylbenzenes were nitrated to the corresponding nitroalkanes as major products in moderate yields with formation of oxygenated products under mild reaction conditions. The carbon-carbon bond cleavage reactions hardly proceeded. ESR, NMR, and IR spectroscopic data show that the vanadium-substituted polyoxometalate, for example, [H4PVMo 11O40], decomposes to form free vanadium species and [PMo12O40]3- Keggin anion. The reaction mechanism involving a radical-chain path is proposed. The polyoxometalates initially abstract the hydrogen of the alkane to form the alkyl radical and the reduced polyoxometalates. The reduced polyoxometalates subsequently react with nitric acid to produce the oxidized form and nitrogen dioxide. This step would be promoted mainly by the phosphomolybdates, [PMo12O 40]n-, and the vanadium cations efficiently enhance the activity. The nitrogen dioxide promotes the further formation of nitrogen dioxide and an alkyl radical. The alkyl radical is trapped by nitrogen dioxide to form the corresponding nitroalkane.

[VO(H2O)5]H[PMo12O40]- catalyzed nitration of alkanes with nitric acid

[VO(H2O)5]H[PMo12O40], which contains vanadyl counter cations and PMo12O40 3-, can act as a catalyst for the nitration of various alkanes including alkylbenzenes using nitric acid as a nitrating agent in acetic acid at 356 K.

Nitration of alkanes with nitric acid catalyzed by N-hydroxyphthalimide

Catalytic nitration of alkanes with nitric acid was first successfully achieved by the use of N-hydroxyphthalimide (NHPI) under mild conditions; the key to the present nitration was found to be the in situ generation of NO2 and phthalimide N-ox

PROCESS FOR THE PREPARATION OF NITRO COMPOUNDS AND METHOD FOR THE REMOVAL OF NITROGEN DIOXIDE

In the invented process for producing a nitro compound, an organic substrate and nitrogen dioxide are reacted in the presence of oxygen or are reacted in a molar ratio of nitrogen dioxide to the organic substrate of less than 1 to yield a corresponding nitro compound. The reaction may be performed in the presence of N-hydroxyphthalimide or other imide compounds. Such organic substrates include (a) aliphatic hydrocarbons, (b) alicyclic hydrocarbons, (c) non-aromatic heterocyclic compounds each having a carbon atom on a ring, which carbon atom is bonded to a hydrogen atom, (d) compounds each having a carbon-hydrogen bond at the adjacent position to an aromatic ring, and (e) compounds each having a carbon-hydrogen bond at the adjacent position to a carbonyl group. This process can efficiently nitrate an organic substrate even under relatively mild conditions.