Reference

Synthesis of dyes from 2-chloro-5-methyl-1,4-phenylenediamine

Synthesis of dyes from 2-chloro-5-methyl-1,4-phenylenediamine. Sebe, Ion; Popescu, Ioan Dan; Ganea, Adriana; Calota, Ioana (Inst. Politeh., Bucharest, Rom.). Ind. Usoara: Text., Tricotaje, Confectii Text., 35(8), 368-71 (Romanian) 1984. CODEN: IUSAAE. DOCUMENT TYPE: Journal CA Section: 41 (Dyes, Organic Pigments, Fluorescent Brighteners, and Photographic Sensitizers) Section cross-reference(s): 40 Reaction of the title compd. (I) [5307-03-9] with bromaminic acid Na salt [6258-06-6] gave II(R1 = SO3Na, R2 = NH2)(III) [96384-10-0], and redn. of III with glucose gave II(R1 = H, R2 = NH2)(IV) [96384-11-1], which was chloroacetylated to form II(R1 = H, R2 = NHCOCH2Cl)(V) [96384-12-2] and then quaternized with C5H5N and ZnCl2 to give II(R1 = H, R2 = NHCOCH2NC5H5.ZnCl3)(VI) [96384-14-4]. III colored wool dark blue; IV colored polyester fibers light blue-violet; V colored polyester fibers violet; and VI colored acrylic fibers violet. All the dyeings exhibited excellent light resistance and good resistance to rubbing and heat. I was prepd. by a series of reactions involving nitrating p-toluidine (VII) [106-49-0], diazotizing nitrated VII, conducting a Sandmeyer reaction on the resulting diazonium salt to give 4-chloro-2-nitrotoluene (VIII) [89-59-8], reducing VIII to 2-amino-4-chlorotoluene (IX) [95-79-4], acetylating IX to 5-chloro-2-methylacetanilide (X) [5900-55-0], nitrating X to 2-acetylamino-4-chloro-5-nitrotoluene [13852-50-1] (plus the 3-nitro isomer), hydrolyzing the isomer mixt., sepg. 2-amino-4-chloro-5-nitrotoluene (XI) [13852-51-2], and reducing XI.

Chloronitrotoluenes

Chloronitrotoluenes. Lerke, Andrzej; Kopka, Ewa; Pilecka, Danuta; Raatz, Bernard; Prokopowicz, Igor; Bembnista, Barbara; Bloch, Henryk (Zaklady Chemiczne "Organika-Zachem", Pol.). Pol. PL 120178 B1 30 Nov 1983, 2 pp. (Polish).There are some reagents with their cas registry numbers 119-32-4 and 89-59-8 are used in this study. (Poland). CODEN: POXXA7. CLASS: IC: C07C079-12. APPLICATION: PL 78-211631 11 Dec 1978. DOCUMENT TYPE: Patent CA Section: 25 (Benzene, Its Derivatives, and Condensed Benzenoid Compounds) Title compds. were prepd. via diazotization of the corresponding amines in the presence of a Cu2+ salt, Cl- ion, and HCl, with addn. of NaNO2 in three portions, the first < 34°, the second < 42°, and the third < 45°. Thus, o-nitro-p-toluidine (I) gave 83% chloro analog II. .