Modified Wolff-Kishner method was written by Huang, Min-Lon;Chung, Tung-Shun;Ku, Tu-Shin;Chow, Wei-Zan. And the article was included in Hua Hseuh Hseuh Pao in 1961.COA of Formula: C9H5BrN2 This article mentions the following:
Successful usage of the Wolff-Kishner reduction was extended to many alkali-sensitive carbonyl compounds through the delayed addition of the alkali reagent. This modification afforded good yields of 1,2-diphenylethane (I) from benzil (II) and benzoin (III), PhCH2CH2CO2H (IV) from PhCH2COCO2H (V), PhCH2CH2CH2CO2H (VI) from PhCOCH2CH2CO2H (VII), and the normal reduction products from other 婵?oxo compounds A lower yield was obtained with furaldehyde (VIII). On the other hand, 闁?oxo compounds do not yield the normal reduction products, but, instead, cyclic N compounds (e.g., IX), while most 婵?闁?unsaturated ketones give rise to cyclopropane derivatives (e.g., X). Thus, 1.5 g. II, 15 ml. diethylene glycol (XI), and 6 ml. 85% hydrazine hydrate (XII) was refluxed 1 hr., the mixture cooled to room temperature, and 1.5 g. KOH was added. The mixture was refluxed 10-20 min. and distilled (to 190闂? liquid temperature) to remove water and excess XII. The residue was refluxed 3 hrs. at 195-200闂? cooled, and diluted with H2O. The white precipitate formed was filtered off, washed, and dried in a desiccator to yield 1.2 g. I, m. 52-3闂?(EtOH). Similarly, 3 g. III, 20 ml. XI, 10 ml. 80% XII, followed by 2 g. KOH, gave 84.8% II. The unmodified Wolff-Kishner method, with the KOH added at the beginning of the reaction, yielded only 50.1% I. Similarly prepared were (product, physical constants, % yield, and starting material given): IV, m. 50-1闂? 76.6, V; VI, m. 49-50闂? 83.3, VII; and 2-methylfuran, b. 62-7闂? n20D 1.4362, 44.7, VIII. On the other hand, 1.5 g. dibenzoylmethane treated with 15 ml. XI, 6 ml. 50% XII, and 1.5 g. KOH by the modified method gave 1.3 g. 3,5-diphenylpyrazole, m. 199-200闂? while 0.5 g. BzCH2CO2H gave 0.22 g. 3-phenyl-5-pyrazolone (XIII), m. 234-5闂? while 1 g. 1,2-dibenzoylethane gave 0.8 g. 3,6-diphenylpyridazine (XIV), m. 221-2闂?(EtOH). Refluxing 5 g. PhCH:CHBz, 25 ml. XI, and 5 ml. 80% XII, and then treating with 3.2 g. KOH, diluting with H2O, and extracting with ether gave 85.8% 1,2-diphenylcyclopropane, b13 171-5闂? n20D 1.5936. Similar treatment of methyl styryl ketone gave 68.1% 1-methyl-2-phenylcyclopropane (X), b. 187-9闂? n20D 1.5222. However, Me2CH :CHAc gave 3,3,5-trimethylpyrazole (IX), b. 159-160闂? n23D 1.4542; HCl salt m. 173-4闂? It was postulated that the low b.p. of IX resulted in a low reflux temperature and prevented further decomposition into the cyclopropane derivative In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6COA of Formula: C9H5BrN2).
5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.COA of Formula: C9H5BrN2
Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles