Notes- An Attempted Synthesis of Phenyl Nitrate

Chaney, Alan; Wolfrom, M. L.

doi:10.1021/jo01066a614

Cited by 16 publications

(10 citation statements)

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“…Purified by column chromatography (petroleum ether/EtOAc, 6/1) as a yellow solid (22.4 mg, 88%); mp 45–46 °C (lit . mp 46–47 °C); IR (KBr): ν = 3350 (OH), 1518 (NO 2 ) cm –1 ; 1 H NMR (CDCl 3 , 500 MHz): δ 10.60 (s, 1H), 8.12 (dd, J 1 = 8.5 Hz, J 2 = 1.5 Hz, 1H), 7.62–7.58 (m, 1H), 7.17 (dd, J 1 = 8.5 Hz, J 2 = 1.5 Hz, 1H), 7.02–6.99 (m, 1H); 13 C NMR (CDCl 3 , 125 MHz): δ 155.1, 137.5, 133.7, 125.1, 120.2, 120.0; MS (EI, 70 ev): m / z (%) = 139 [M + ].…”

Section: Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed Aromatic C–H Bond Nitration Using Removable Directing Groups: Regiospecific Synthesis of Substituted o-Nitrophenols from Related Phenols

Zhang

Ren

et al. 2014

J. Org. Chem.

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A general and regiospecific transformation of substituted phenols into the related o-nitrophenols has been achieved via a three-step process involving the palladium-catalyzed chelation-assisted ortho-C-H bond nitration as the key step. In the process, 2-pyridinyloxy groups act as removable directing groups for the palladium-catalyzed ortho-nitration of substituted 2-phenoxypridines, and they can be readily removed in the subsequent conversion of the resulting 2-(2-nitrophenoxy)pyridines into 2-nitrophenols.

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Section: Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed Aromatic C–H Bond Nitration Using Removable Directing Groups: Regiospecific Synthesis of Substituted o-Nitrophenols from Related Phenols

Zhang

Ren

et al. 2014

J. Org. Chem.

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“…pare phenyl nitrate from phenyl chloroformate and silver nitrate resulted in a 64% yield of o-nitrophenol (118).…”

Section: O O C02c2hsmentioning

confidence: 99%

The Chemistry of Chloroformates

Matzner¹,

Kurkjy²,

Cotter³

1964

Chem. Rev.

139

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“…For example, studies reported in [15,16] revealed no differences in their catalytic properties. Differences in the catalytic properties of the high and low molecular weight forms of ADA have been described in only one of our previous studies [14]. This study compared the catalytic properties and particularly the inhibition of two low molecular weight and three high molecular weight forms of ADA from several bovine tissues.…”

Section: Experimental Biological Sectionmentioning

confidence: 90%

“…Electrophoretic analysis showed that the preparation of the high molecular weight form of bovine kidney ADA (molecular weight 280 -300 kDal) [14] was 90% pure. Adenosine was obtained from Sigma Ltd. (USA).…”

Section: Experimental Biological Sectionmentioning

confidence: 99%

Synthesis of 2-(4-substituted phenyl)-3-[4-substituted piperazino(piperidino)]propan-1-ol dihydrochlorides and their effects on adenosine deaminase activity

et al. 2011

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Aminomethylation of 4-substituted acetophenones yielded a series of b-amino-4-substituted propiophenones. Reduction of these with lithium alumohydride in dry ether produced 1-(4-substituted phenyl)-3-[4-substituted piperazino(piperidino)]propan-1-ols, which were then converted to the corresponding dihydrochlorides. The abilities of these compounds to inhibit adenosine deaminase, a key enzyme in purine metabolism in living organisms, were studied. Some of the compounds had quite marked inhibitory effects on the enzyme. The abilities of the compounds synthesized here to inhibit adenosine deaminase were found to depend on their structure. It is of note that virtually all the compounds inhibited the high molecular weight form of the enzyme to a significantly lesser extent than the low molecular weight form.

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Notes- An Attempted Synthesis of Phenyl Nitrate

Cited by 16 publications

References 0 publications

Palladium-Catalyzed Aromatic C–H Bond Nitration Using Removable Directing Groups: Regiospecific Synthesis of Substituted o-Nitrophenols from Related Phenols

Palladium-Catalyzed Aromatic C–H Bond Nitration Using Removable Directing Groups: Regiospecific Synthesis of Substituted o-Nitrophenols from Related Phenols

The Chemistry of Chloroformates

Synthesis of 2-(4-substituted phenyl)-3-[4-substituted piperazino(piperidino)]propan-1-ol dihydrochlorides and their effects on adenosine deaminase activity

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