9(10H)-アクリドン

解説C13H9NO(195.22)．アクリドンは，ジフェニルアミン-2-カルボン酸を塩化ホスホリルとともに加熱し，生成した9-クロロアクリジンを希塩酸で処理すると得られる．黄色の結晶．融点354 ℃．エタノールに易溶，エーテル，ベンゼン，クロロホルムに可溶．亜鉛末還元によって，アクリジンに還元される．インダンスレン系染料，および蛍光物質の合成原料として用いられる．森北出版「化学辞典（第2版）

用途有機合成原料。

使用9(10H)-Acridone is a catabolic product of carbamazepine (C175840) metabolite and can be used as a fluorescent tag for antibody catalysis.

純化方法Dissolve ~1g in ca 1% NaOH (100mL), add 3M HCl to pH 4 when acridone separates as a pale yellow solid with m just above 350o (sharp). It can be recrystallised from large volumes of H2O to give a few mg. It is soluble in 160 parts of boiling EtOH (540 parts at 22o) [Albert & Phillips J Chem Soc 1294 1956]. Afew decigms are best crystallised as the hydrochloride from 400 parts of 10N HCl (90% recovery) from which the free base is obtained by washing the salt with H2O. A small quantity can be recrystallised (as the neutral species) from boiling AcOH. Larger quantities are best recrystallised from a mixture of 5 parts of freshly distilled aniline and 12.5 parts of glacial acetic acid. Acridone distils unchanged at atmospheric pressure, but the boiling point was not recorded, and some sublimation occurs below 350o. It has UV: 399nm. [see max Albert, The Acridines Arnold Press pp 201, 372 1966; for pKa see Kalatzis J Chem Soc (B) 96 1969, Beilstein 23/9 V 7.]