Isatogens. V. Hydroxyhydroquinol derivatives of the isatogen series was written by Ruggli, Paul;Leonhardt, Werner. And the article was included in Helvetica Chimica Acta in 1924.Product Details of 5367-32-8 This article mentions the following:
Thiele’s reaction in which a hydroxhydroquinol is formed from p-C6H4O2 and Ac2O containing some H2SO4 (Ber. 31, 1247) may be applied to the isatogen series. Thus when 3 g. 6-nitro-2-phenylisatogen is added to 15 cc. Ac2O containing 0.25 cc. concentrated H2SO4 and warmed to 50° for 15 min., there results, in addition to 1 g. of a by-product to be described later, 2 g. (45%) of 1,3,5-triacetoxy-2-phenyl-6-nitroindole (I), bright yellow, m. 194-5°. Aqueous alkali gives a deep red solution; concentrated H2SO4 gives a deep violet solution containing III. Boiling 2 g. I with 20 cc. EtOH and 1.25 cc. concentrated HCl about 30 min. gives the 1,3-Ac2 derivative, orange-yellow, m. 214-5° (70% yield); with concentrated H2SO4 it gives the same violet solution as I. The 5-chloroacetoxy derivative is yellow and m. 156-8° (decomposition). The 5-MeO derivative (II), greenish yellow, m. 221-2°, results by the action of CH2N2. Concentrated H2SO4 reacts with I to give 2-phenyl-5-hydroxy-6-nitro-3-ketoindolenine (III), brick-red, m. 188°; very dilute alkali gives an emerald-green solution, from which black flakes soon sep. A large excess of H2NOH.HCl gives the oxime (IV), red, m. 280° (decomposition), which gives a Me ether, dark red, m. 172°, with Me2SO4; this with Ac2O-H2SO4 gives the 5-Ac derivative, brick-red, m. 152°. The 5-MeO derivative (V), dark red, m. 205°, results by the action of concentrated H2SO4 upon II; warmed with aqueous alkali, it gradually decomposes Ac2O regenerates II. The oxime (VI), orange-red, m. 263-4°, whose Me ether is deep red and m. 157°; this is also formed from IV and CH2N2. Oxidation of VI in AcOH with CrO3 gives 2-phenyl-3,6-dinitro-5-methoxyindole, bright yellow, m. 303-6° (decomposition), in 40-45% yields, while oxidation of V gives 4-nitro-5-methoxybenzoylanthranilic acid (VII), golden yellow, m. 272°. Heated with H3PO4 up to 170°, VII gives 2-amino-4-nitro-5-methoxybenzoic acid, violet-black, m. 217-8°; the aqueous solution is orange-red. 4-Amino-5-methoxybenzoylanthranilic acid, decompose 200°, results by the reduction of the Na salt of VII by H and Ni; the 4-Ac derivative decomposes 275°. The reduction of the diazo compound yields 5-methoxybenzoylanthranilic acid, m. 200°, which was synthesized from 2-nitro-5-methoxytoluene, yellow, m. 50°, through reduction with Sn and HCl and subsequent treatment with NaOH and BzCl, yielding the 2-benzoylamino-5-methoxytoluene, m. 200°, and oxidation with KMnO4. The 3-methoxybenzoylanthranilic acid, prepared in a similar manner, m. 204.5°, but depressed the m. p. of the 5-derivative 25°. 2-Nitro-6-methoxytoluene, yellow, m. 52°. 2-Benzoylamino-6-methoxytoluene, m. 177°. 6-Methoxybenzoylanthranilic acid, m. 120°. The action of SnCl2 in AcOH saturated with HCl upon II gives 2-phenyl-3-acetoxy-5-methoxy-6-aminoindole, m. 212°; with Ac2O and concentrated H2SO4 this forms 1-acetyl-2-phenyl-3-acetoxy-5-methoxy-6-diacetaminoindole, m. 220°. Me isatogenate treated with Ac2O and H2SO4 gives a yellow compound, C16H15O8N, m. 193-5°, which may be the corresponding triacetoxyhydroquinol derivative In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Product Details of 5367-32-8).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Product Details of 5367-32-8
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem