Adamantane → 1-Nitroadamantane

HRID 992147

Reaction equation

HRID 992147 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:11][N:12]1C(=O)C2=CC=CC=C2C1=O.[N+]([O-])=[O:24].[N]=O>C(O)(=O)C.C(#N)C1C=CC=CC=1>[N+:12]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)([O-:11])=[O:24].[C:1]12([OH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

8

Reactant 4

HCID 9238Adamantane2×HCID 10665N-HydroxyphthalimideHCID 145068Nitric OxideHCID 178526396Nitrogen Dioxide

Product 2

HCID 641521-AdamantanolYield 6%HCID 641651-NitroadamantaneYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7505BenzonitrileSolvent

Procedure

Into a flask, 1 mmole of adamantane, 0.1 mmole of N-hydroxyphthalimide, 2 ml of nitrogen dioxide (N2O), 6 ml of benzonitrile (6 ml) and 1.2 ml of acetic acid were added and stirred for 12 hours at 60° C. in an atmosphere of nitrogen monoxide (NO). The reaction products were analyzed by gas chromatography, and, as a result, the conversion of adamantane was 98%, nitroadamantane (yield 68%), adamantanol (yield 6%) and acetyloxyadamantane (yield 4%) were formed.

Sources & evidence

ORD record
ord-21b5cc6f392b455aa5422c0c24119d5f
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Linked notes

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