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.

Selective nitration of 5-chloro-2-methylaniline

Selective nitration of 5-chloro-2-methylaniline. Terc, Jiri (Vyzk. Ustav Org. 13852-51-2 and 13852-52-3 are also occured in this study. Synt., Pardubice, Czech.). Chem. Prum., 26(12), 641-4 (Czech) 1976. CODEN: CHPUA4. DOCUMENT TYPE: Journal CA Section: 25 (Noncondensed Aromatic Compounds) Section cross-reference(s): 40 Nitration of 2,5-Me(Cl)C6H3NHR (R = p-tosyl, Ac) with HNO3-H2SO4 afforded the 5-chloro-2-methyl-4-nitrophenyl amides I, along with traces of the 2-nitro isomers. Hydrolysis of I (R = acyl) afforded I (R = H), which were reduced to the diamines. .