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Adamantane → 1-Nitroadamantane

HRID 992144
Notes
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Reaction equation

HRID 992144 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:24]>C(O)(=O)C>[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 9238Adamantane2×HCID 10665N-HydroxyphthalimideHCID 145068Nitric Oxide

Product 2

HCID 641521-AdamantanolYield 17%HCID 641651-NitroadamantaneYield 30%

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Procedure

Into a flask, 1 mmole of adamantane, 0.05 mmole of N-hydroxyphthalimide and 5 ml of acetic acid were added to mix and then the flask was equipped with a gas bag (about 1L) of nitrogen monoxide NO. The mixture was reacted for 8 hours at 100° C. with stirring. The reaction products were analyzed by gas chromatography, and, as a result, The conversion of adamantane was 95%, and nitroadamantane (yield 30%), adamantanol (yield 17%) and acetyloxyadamantane (yield 33%) were formed.

Workup

  1. additionto mix
  2. customThe mixture was reacted for 8 hours at 100° C.

Sources & evidence

ORD record
ord-936800d461a648ebb2b88230cf9f8568
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06468487B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes