Anthracene 9-carboxylic acid chloride

Anthracene, at 180-200 "C, gave some anthracene-9-carboxylic acid chloride (10.1) on reaction with COClj in the presence of aluminium(III) chloride [811a], whilst at 240-250 C, lO-chloroanthracene-9-carboxylic acid chloride (10.2) was formed [153b]. 

Typical procedure. Anthracene 9-carboxylic acid chloride 1341 [1013] A solution of anthracene 1340 (5 g) and oxalyl chloride (30 ml) in nitrobenzene (150 mL) was heated to 120 °C, and then the temperature was raised to 240 °C over a period of... 

The same nonpolar conformation can be achieved by conversion to bicyclic structures. 1,4-Cyclo-addition of ethylene to anthracene-9-carboxylic acid gives acid 68. Successive conversion to the N-methylamide, via the acid chloride, followed by reduction with lithium aluminum hydride produced... 

It has recently been suggested that stimulation of gastric acid secretion across the apical membrane of the gastric parietal cell predominantly reflects the insertion of an active potassium and chloride transporter/ channel rather than direct activation of HVK -ATPase. However, the mechanisms involved in and Cl transport into the gastric parietal cell are still controversial. The presence of a Cl channel in the apical membrane has been confirmed by using established d channel blockers. In vitro in rabbit isolated gastric parietal cells, 9-anthracene carboxylate and the more potent diphenylamine-2-carboxylate inhibit gastric acid formation concen-tration-dependently irrespective of the kind of stimulation [181]. Thus Cl channel blockers can be defined as indirect HVK -ATPase inhibitors. 

Recently, Bayliss et al. [132] described the synthesis of anthracene-9-carbonyl chloride and its aplications as a label for fluorescence and UV absorbance detection of hydroxy compounds. The preparation and properties of esters of short-chain alcohols, diols, trichothecene mycotoxins and sterols were investigated. Anthracene-9-carbonyl chloride was prepared from commercial anthracene-9-carboxylic acid. Derivatization was carried out in acetonitrile free from water or active hydrogen compounds. The reaction rate was dejjendent on the structure of the alcohol. The derivatization of diethylene glycol was complete at ambient temp>erature within 10 min (0.25 M reagent) or 30 min (0.1 M reagent) without a catalyst, but required 1 h for diolesteroL testosterone and the trichothecene T-2 toxin. For sterically hindered alcohols such as t-butanol and 17a-methyl-testosterone, more than 10 h, or refluxing for 1 h, was needed to complete the reaction. The derivatives had absorption maxima at 250 run. Both normal and reversed phase HPLC were applied to the separation of the derivatives. 

Direct introduction of the carboxyl group into an aromatic ring is accomplished with urea hydrochloride, phosgene, oxalyl chloride, or carbon dioxide. Carboxylation of benzene is effected in 15-58% yields by treating with liquid phosgene and aluminum chloride. No catalyst is required in the conversion of dimethylaniline and phosgene to p-dimethyl-aminobenzoic acid (50%). 9-Anthroic acid (67%) is prepared from anthracene by heating to 240° with oxalyl chloride and nitrobenzene. ... 

Direct introduction of the carboxyl group into the aromatic ring has also been accomplished with phosgene and oxalyl chloride. Thus, for example, 9-anthroic acid is prepared in 67% yield from anthracene by heating to 240°C with oxalyl chloride in nitrobenzene [12]. 

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